Enantioselective synthesis of a 3'-dephenylcryptophycin synthon

Mari Jean Eggen, Gunda I. Georg

Research output: Contribution to journalArticle

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Abstract

An enantioselective synthesis of tert-butyl (5S,6R)-(E)-5-tert- butyldimethylsilyloxy-6-methyl-2,7-octadienoate, a precursor for the synthesis of the antimitotic macrolides cryptophycin A and arenastatin A (cryptophycin-24), is presented. The key step in the reaction sequence features a crotyl boration that sets both stereocenters that become the C16 hydroxyl and C1' methyl in the cryptophycins. Homologation of the terminal olefin via a Heck reaction is presented.

Original languageEnglish (US)
Pages (from-to)3177-3180
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume8
Issue number22
DOIs
StatePublished - Nov 17 1998

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