Friday Fun: Sweet Cardamom (Peroxide)

Rice pudding. Ginger snaps. And...malaria?

That's what'll be going through my head next time I cook with cardamom, thanks to Tom Maimone and coworkers (UC-Berkeley) and their under-the-wire JACS ASAP from yesterday afternoon. The title and abstract scratch all the Baran lab alumni itches: 1) biosynthetically inspired, 2) novel mechanisms, 3) scalable, 4) just four steps! And hey, we're making stable endoperoxides, which all the cool kids are into nowadays.



Not their actual abstract graphic...

As Maimone points out, the latent symmetry of the final product offers a really neat assembly strategy. The group McMurrys together two units of (-)-myrtenal, then hits it with singlet oxygen, initially forming a 6-membered endoperoxide they fragment / rearrange with base. A gentle oxidation (DMP) sets them up for the wild step: stitching together a 7-membered endoperoxide using Mn(III)*, a radical source, a silane reducing agent, and even more oxygen. Simple phosphine reduction knocks down the last hydroperoxide into an alcohol, and the whole target (7 stereocenters!) falls out as a single stereoisomer.

Pretty sweet.

P.S. - Since the group's made over half a gram in just this first push, I'd assume an efficacy paper against live Plasmodium parasite hot on the heels of this one...

*We're apparently already calling this the "Shenvi catalyst"...wasn't this only two months ago?

Exactly Like Cooking - Review of "Yes, Chef"

It's been a while since I've read a book I couldn't put down. Especially one that blends two of my favorite subjects: cooking, and indentured servitude "making your bones" in a tradition-bound hierarchy.

Marcus Samuelsson's Yes, Chef: A Memoir reads like a grad school recap...(in a good way!)

Credit: Random House

For those unfamiliar with Chef Samuelsson - owner of the Red Rooster in Harlem and former executive chef of Aquavit - his story reads like a modern fairy tale. Adopted from Ethiopia at 5, into a white-collar Swedish home outside Goteborg. Attended a technical school (Mosesson), where he fell in love with culinary arts. As a journeyman chef, he cooked his way through a series of European restaurants (Belle Avenue, Victoria Jungfrau, Elisabethpark, Georges Blanc), some cruise ships, and a long stint in New York City, where he finally decided to land. Along the way, he's taken some turns on TV, first on Top Chef: Masters and recently as a judge on Chopped. He's cooked at a State Dinner for President Obama.

Samuelsson's writing, humble yet descriptive, makes you truly see the food in front of you. You can feel the pain and grind of kitchen life, from cuts, burns, and scrapes to the deeper emotional wounds wrought by oppressive managers and head chefs with attitude. Samuelsson emerges from the book less a 'foodie hero' than a grizzled vet of the restaurant scene.

Of course, the parts I most appreciated paralleled my life as a bench-bound synthetic chemist. Kitchen shifts, like lab work, demand long hours, dedication, and a willingness to learn every facet of the job, from "front of house" to garde manger, herb garden to chef de partie. Chemists, too, find their jobs easier when they make a point of practicing skills to the point of subconscious performance - filleting fish or de-boning duck become as automatic as pulling pipettors or running rotovaps.

I enjoyed the concept of a stage, a tradition between restaurants (p.74):

"To be sent away was the highest honor: It meant that you would be sent off to spend a week, a month, or a season doing a stage, which was an unpaid apprenticeship ...the idea was that you'd either come back, bringing those new techniques and skills you'd picked up with you, or or your boss's kindness would come back to him someday."

(Doesn't this sound like a visiting researcher position, or perhaps a short postdoc?)

Less amusing, though, was the metric for success in moving up the cooking ladder (p. 165):

"Don't draw attention to yourself. I know it sucks, but try to be as small as possible."

"...to get ahead in that culture, you have to completely give yourself up to the place. Your time, your ego, your social life, your relationships, they are all sacrificed. It's a daily dose of humility most Americans find difficult to swallow."

(Uncomfortably close to graduate school, right there).

Finally, Samuelsson does not understate the role luck and failure play in shaping one's career. Multiple random events, albeit tragic ones - car accidents, deaths, missed contacts - propelled him into his current life. As with progress through a long total synthesis, failure too can drive you to seek out new ideas, or at least discard the bad ones fast.

I'd recommend this book to anyone with the dual food / chemistry interest; I think you'll find a lot of familiar territory. A real page-turner.

Happy Reading, Happy Eating, Happy Friday!
See Arr Oh

Exactly Like Cooking - Pancakes!

Continuing our series to put more money into grad student wallets, through the power of cheap -but nutritious! - leftover-generating food.

Well, it's never a bad time for pancakes. Just about 10 minutes from reading this, you, too, could be chowing down on a short stack...and it requires relatively few ingredients. You probably have them all just hanging around.

Fluffy Pancakes (Prep Time: 10 minutes)
Adapted from Kris, at allrecipes.com

Equipment - Large pan or griddle, spatula, wooden spoon, measuring cup, measuring spoons, large bowl, small bowl.

Base Ingredients (about 6 pancakes) - 3/4 cup milk
2 tablespoons vinegar

1 cup whole wheat flour
2 tablespoons white sugar
1 teaspoon baking powder
1/2 teaspoon baking soda
1/2 teaspoon salt
1/2 tsp oil

1 egg
1 tbsp butter


Fun Part - vanilla, cocoa, cinnamon, nutmeg, cloves, ginger (to taste)
nuts, raisins, oats, other fruits or grains (to taste)

Procedure - Heat skillet / pan to medium heat. Pre-mix the milk and vinegar in large bowl, set aside 5 minutes; this simulates buttermilk, so if you'd rather, you can experiment with combos of kitchen acid / milk here: lemon juice, cider vinegar, etc. Now, add egg, oil, and butter to milk mixture, with stirring. 


Mix the first five dry ingredients together in a smaller bowl. Slowly add these dry ingredients to milk mixture, with stirring, over about 1 minute. Now's your chance to "personalize" your pancakes - spices, nuts, grains, chocolate chips, or fruits are all welcome. We at Just Like Cooking prefer combos like strawberry ginger, cinnamon pecan, raisin oat, or cocoa banana.


Remember that hot pan? Grease it lightly with spray or butter, and ladle on small portions (think about 1/4 c, or maybe 60 mL). The cakes will spread out slightly, begin to brown on the edges, and form small bubbles on top. After about 2 minutes, lift up a side - if it's golden brown, flip 'em all. Cook about 30 seconds on the other side, and transfer to plate for serving. 


But wait! Your pancake personalization hasn't yet ended...feel free to top these off with maple syrup, butter, peanut butter, Nutella, berry syrup, fresh fruit, powdered sugar, or black sesame seeds.


Total Cost: Dry ingredients ($1.00), Egg ($0.25), milk ($0.50), oil / butter ($0.25), spices ($0.50), additives ($1.00) = $3.50, or about $1.75 / 3 pancake serving.

Press Release Supplement

As part of my new editorial gig over at Nature Cooking, I've had sit-downs with all the major factions in the company, including the fine folks over at Nature Protocols. They were kind enough to suggest a theme for our first issue; apparently, that's chemistry cookies!

Credit: Nature Protocols, via "The Twitter"

In an attempt to please my new colleagues, I scoured the Electrical Highway for at least 5 minutes, until I found these critical lab instruments:

Scientific Cookie Cutters | Credit: thinkgeek.com

Oddly, the strychnine and maitotoxin shapes were on back order....c'est la vie.

Exactly Like Cooking - Black Beans, Rice, and Plantains

Continuing our series to put more money into grad student wallets, through the power of cheap but nutritious (and leftover-generating) foods!


This recipe comes to you by way of three Cuban / Jamaican food staples: plantains (thick, fibrous banana-like fruits), black beans, and rice. The prep time is a bit longer, but, as a trade-off, you get quite a few extra meals here.

Picture this, but with rice...
Source: Allrecipes.com

Black Beans, Plantains, and Rice (Prep Time: 20 minutes)
Equipment - Small pan, small pot, one more pot (or rice cooker), wooden spoons (2), measuring cup (1 c), sharp knife, cooking oil.


Ingredients - 1 can black beans (Goya, Bush's, store brand)
1 green pepper
0.5 onion
0.5 tomato
1 box frozen plantains (Goya, Publix, Wal-Mart brand, etc.)
1.0 c rice
1.5-2.0 c water
some butter (2 tbsp)
some brown sugar (4 tbsp)
some plain Greek yogurt (1 tbsp)
some shredded cheese (handful)
spices: cumin, garlic, cilantro, parsley, curry powder, salt, pepper, adobo, hot sauce (all to taste)


Procedure - Get that rice cooking, either by loading it into your rice cooker, or by boiling water on high, stirring in the rice, then reducing heat to medium-low and covering with a lid. Meanwhile, dice up (cut into small pieces) pepper, onion, and tomato, then load into a pot with a small amount (2 tsp) of oil on medium heat, uncovered. Stir every 2 minutes or so, until you hear popping sounds and see steam slowly rising from the pot. Add the black beans (no need to rinse 'em, just dump it in!), and stir occasionally, until bean / veg mixture begins to simmer. If you want, now's the time to add your spices (see above list).


OK, plantain time! Heat a few spoonfuls of oil in your small pan, on medium to medium-high heat. While the oil heats, gently defrost your plantains, usually with 1 minute of microwave heating (or by leaving them out for a few hours). Begin to fry the partially-defrosted plantains in the hot oil, turning often, until they take up some of the oil and begin to brown. Reduce heat to low, add butter and brown sugar (maybe also some cinnamon and hot sauce?), turn often until plantains are sticky and deep brown. 


By this point, the rice should be done. Drain (if in a pot), scoop out onto plates, spice with parsley / pepper / salt. The beans should have lost some moisture, and should be more like a thick soup. Grab about 1 cup of the mixture to cover your rice. Add one or two of the fried, sugared plantains on top, cover with hot sauce and Greek yogurt (replaces sour cream), and some shredded cheese. Should make four (4) total servings.


Total Cost: Beans ($1.00/can) + Rice ($0.50 / cup) + Plantains ($1.75 / box) + veggies ($1.50) + Brown sugar ($0.35) + Butter ($0.40) + Dairy Additives ($0.75) + Spices ($0.50) = $6.75, or about $1.69 / serving.

Exactly Like Cooking - Microwave Bagel Sandwich

OK, starving grad students everywhere, Round 2!


For the first few years of school, I got by with what I thought I could best afford: Pop-tarts, cereal, trail mix, yogurt, or corn meal mush. I realized (much later) that these foods, cheap though they were, wouldn't sustain me for the long morning push of reaction set-ups, group meetings, and seminars. It's also not a great idea to supplant the need for proper nutrition with more coffee - not if you want to sleep at night! (Do chemists sleep, anyway?)


Thus began my long experiment to find alternative (cheap!) breakfast ideas. Early on, I realized that the little café a few blocks from campus had it right: they microwaved egg mixture, slapped some cheese on it, and popped it onto a bagel...and charged you $4.50! I thus embarked on a quest to learn how to construct a bagel sandwich for myself, using only what was in our lab break room: a fridge, plastic forks and spoons, a microwave, and a toaster.

Delicious and Cheap!
Source: For the Love of Cooking

Microwave Bagel Sandwich (Prep Time: 5 minutes)
Equipment - paper towel or napkin
small, round poly container (think side-dish containers from take-out food!)
cooking spray


1 egg
5-10 mL (1/2 oz.) of milk
handful shredded cheese 
pinch of salt, pepper, parsley, curry powder, or hot sauce
1 bagel, toasted


Procedure - Spray inner surface of small plastic dish with cooking spray. Mix egg and milk together with plastic fork in dish, add spices to taste. Fold paper towel in half lengthwise, and cover dish by "wrapping" towel over the top and tucking ends under the bottom (in case egg explodes from excess heat).


Place bagel in toaster and commence toasting. In the meantime, set microwave (assumes a 120V, 2 Amp microwave) for a single cycle of 48 seconds at 60% Power. Remove dish, lightly "shake" to ensure cooking is even, re-cover with towel, and place in for a second cycle of 50 seconds at 90% Power. Now add your cheese, and microwave one last time (uncovered, this time) for 10 seconds at full power. This should melt the cheese. 


Did your bagel finish toasting? Great! Take one half of the bagel, and place it over the plastic dish. Invert the entire thing (a "puck" of cooked egg should slide out), and top with final bagel slice. If this still isn't enough food, consider adding some spinach leaves, apple slices, or microwaved bacon / ham to augment.


Total Cost: Bagel ($0.50-$0.80, in pk. of six), + egg ($0.20) + cheese ($0.25) + milk ($0.10) = About $1.25 per serving. 

Exactly Like Cooking – Corn Meal Mush

Since I started this blog last year, I’ve looked back often at the tongue-in-cheek title. I thought that, like Derek’s delectable experiments, perhaps I should chime in with an offering of my own. However, I thought I’d aim for the opposite end of the culinary spectrum: the starving grad student.

"Piled Higher and Deeper" by Jorge Cham - www.phdcomics.com

Back in school, I not so fondly remember weekends where I had about $5 in my pocket until my next stipend check came in. Sometimes, a trip to McDonald's seemed like a fancy night out. Most of the time, though, I fell back on some tried-and-true favorites: soup, frozen broccoli, ramen noodles, or oatmeal.

But in terms of cost : hunger ratio, I never found a better recipe than this, a See Arr Oh family classic:

Fresh from the pot...so cheap, so good!

Corn Meal Mush (Prep time 10 minutes, serves 4)

3 cups boiling water

1 cup finely-ground yellow corn meal (I prefer Quaker or Goya, but any fine meal will do)

1 tsp salt

1 cup cold water

Procedure – Bring 3 cups of water to a rapid boil. In a separate bowl, pre-mix the cold water, salt, and corn meal together until a loose suspension (no clumps!) forms. Quickly pour the mixture into the boiling water with stirring, and reduce the burner heat to medium-low. Cover pot. Simmer the thickening corn mixture for about 7 minutes, stirring occasionally.

We serve this warm at breakfast, with butter, pepper, and white sugar. I could imagine it seasoned to taste for dinner (cumin, hot sauce, red pepper, soy), or perhaps as a side dish (paprika, parsley, thyme) to a meat or vegetable.

Total Cost: $0.30-0.50 per serving, depending on spices and seasonings