Stereoselective synthesis of (E)-beta-tributylstannyl-alpha,beta-unsaturated ketones: Construction of a key intermediate for the total synthesis of zoanthamine

Thomas Eiland Nielsen, David Ackland Tanner

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

(E)-beta-Trialkylstannyl-alpha,beta-unsaturated ketones are readily available from secondary propargylic alcohols via a two-step sequence involving highly regio- and stereoselective Pd(0)-catalyzed hydrostannation followed by mild oxidation (TPAP). The methodology has been applied to the synthesis of enantiomerically pure enone 12 which is a key intermediate for the total synthesis of zoanthamine, a structurally complex marine natural product.
Original languageEnglish
JournalJournal of organic chemistry
Volume67
Issue number18
Pages (from-to)6366-6371
ISSN0022-3263
Publication statusPublished - 2002

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