(-)-Aplysiallene
September 3rd, 2007 by Natural Product
Hello 
First, some nice Total Synthesis of (-)-Aplysiallene published in Organic Letters.
This compound was found in red alga Laurencia okamurai Yamada (in 1985) and in sea hare Aplysia kurodai (in 2001). Retrosynthetc Analysis of (-)-Aplysiallene is presented below. Initially stereochemistry of (-)-Aplysiallene was opposite to stereochemistry presented above. Structure of that target was revised thanks to NMR.
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.gif "Retrosynthesis of aplysiallene(2)")
.gif "Retrosynthesis of aplysiallene(3)")
And the way in which real structure of (-)-Aplysiallene was synthesized is shown:
.gif "Synthesis of (-)-Aplusiallene")
.gif "Synthesis of (-)-Aplusiallene")
.gif "Synthesis of (-)-Aplusiallene")
.gif "Synthesis of (-)-Aplusiallene")
.gif "Synthesis of (-)-Aplusiallene"){kind=small}
.gif "Synthesis of (-)-Aplusiallene")
It’s very interesting to me the use of oxygen as oxidant supported by cobalt-based Mukaiyama catalyst. I’m wondernig about mechanism of that oxidation…
For more information see: J. Wang, B. Pagenkopf, Organic Lett., 2007, 9, 3703.
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