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Approach towards C12 oxo analogues of the side chain of pumiliotoxin B/allopumiliotoxin 339A and B

✍ Scribed by John M. Gardiner; Philip E. Giles; Marı́a Luz Martı́n Martı́n

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 92 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01071-7

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✦ Synopsis

A route towards the synthesis of analogues of pumiliotoxin and allopumiliotoxin side-chain is described. The C15,C16 diol was introduced by asymmetric dihydroxylation using AD-mix b of C10,C17 enynone intermediate 14, or of C13,C17 precursor 17, or by using a chiron-based route from 24. The trisubstituted alkene functionality was established using arylthio conjugate addition to ynones 16 and 27, followed by a copper-catalyzed stereoretentive reaction with methylmagnesium bromide. The approach enables access to C12 oxo systems and offers an approach towards new C14 analogues.

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