Synthetic studies on perophoramidine and the communesins: Construction of the vicinal quaternary stereocenters

Jae Hong Seo, Gerald D. Artman, Steven M. Weinreb

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Abstract

An efficient synthetic strategy for installation of the two vicinal quaternary carbon centers of the communesins is reported. Key steps include the O-allylation/Claisen rearrangement of spirolactone systems, which are formed by tandem intramolecular Heck cyclization/carbonylation. Substituent and solvent effects on the stereochemical outcome of the Claisen rearrangements have been examined. The stereochemical assignment of the allyl spirolactone previously reported as 17 has now been revised to 31, which has the communesin relative configuration at the quaternary carbons. Key C-allyl spirolactone 59 bearing functional handles required for the communesin core has been constructed with a 9.8:1 diastereomer ratio.

Original languageEnglish (US)
Pages (from-to)8891-8900
Number of pages10
JournalJournal of Organic Chemistry
Volume71
Issue number23
DOIs
StatePublished - Nov 10 2006

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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