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Synthesis of functionalized bicyclo[3.2.1]octan-6-ones for diterpenoids: allylsilane directed Pummerer reaction: insertion reactions of diazoketones

✍ Scribed by Philip Magnus; Trevor Rainey; Vince Lynch

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 144 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00336-8

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✦ Synopsis

The sulfide 5 underwent Pummerer cyclization to give 6, whereas the allyl silane analog 10 produced the bicyclo[3.2.1]octanones 11 and 11a. Extension of this methodology to 15 resulted in 16 without the necessity for allyl silane activation. The intermediate diazoketone 14 on treatment with BF 3 •OEt 2 gave 17, 18 and 19, whereas the saturated adduct 22 on treatment with Rh 2 (OAc) 4 gave 23.

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