Avrainvillamide and Stephacidins A & B
Baran, Hafensteiner, Ambhaikar, Guerrero, and Gallagher. JACS, 2006, ASAP. DOI: 10.1021/ja061660s.
Detailing their syntheses of three related natural products in this article, Phil Baran’s group have been working rather hard on this funky dimeric natural product. Created via the spontaneous dimerisation of avrainvillamide, their synthesis of this series is incredibly compact. To the business end:
Thus, the synthesis plan now requires a construction of the monomeric unit, which begins with an impressive piece of new technology. Using palladium catalysis, they have developed a route to substituted tryptophans from simple precursors, inspired by some work published by Merck (DOI: 10.1021/jo970278i). After optimisation, they isolated the desired tryptophan in 75%.
Using this product, deprotection/protection led to the precursor for their benzopyran formation, which, itself, was created by propargylation of the free alcohol using an interesting literature procedure (doi:10.1016/S0040-4020(03)00862-7), involving generation of a vinylidene carbene generated in situ from propargylic carbonate, base, and catalytic CuCl.
All in, this is some pretty neat work. I urge you to read the paper (all sixteen pages!) – it’s top stuff!
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I have to admit… I’m impressed by your mad Chemdraw skills
finally got through it. lots of cool chemistry here. wish there were more papers like this.
check myers paper a year ago.
what is the deal with all those “first author” thing?
Looks like you have too much time on your hands dear boy! Back to your fumehood.
You know, you guys in lab 122 really underestimate me – Do Not Underestimate The Power Of Tot. Syn.!! And posting as Jon whilst he’s in a meeting doesn’t leave me with too much guessing to do…
check this out guys hahahaha lololol SEXY Scientist profiles. And guess what…Phil is one of them
http://sexyscience.blogspot.com/2006/04/profile-1-dr-phil-baran.html
i’ve heard nothing but good things about him personally.
I have met him before, he is a nice and passionate guy (passion about what he is doing)
I don’t know if anyone comments from the Baran group, but lets just say that his name is normally mentioned fairly high up in the stats for the website…
which website?
Umm, this one!!
[...] family, which has appeared in two previous posts here, one by Robert Williams, the other by Phil Baran. However, there doesn’t appear to be a ‘family name’ – they’re just [...]
SPAMster, SPAMster, SPAMster ALERT!!!!!!!! :/