Further studies on total synthesis of sarain A. Efforts toward annulation of the macrocyclic rings

Osamu Irie, Kiyohiro Samizu, James R. Henry, Steven M. Weinreb

Research output: Contribution to journalArticle

51 Scopus citations

Abstract

Studies have been conducted on testing strategies for annulation of the two macrocyclic rings onto the central tricyclic nucleus of sarain A (1). In particular, methodology has been developed for introduction into the core of C-3' and C-3 substituents, which are necessary for construction of the 'eastern' and 'western' macrocyclic rings of 1, respectively. Formation of the western ring has been successfully addressed via a ring-closing olefin metathesis strategy utilizing the Grubbs ruthenium catalyst. With this macrocyclization approach, a key intermediate lactam has been prepared which will be utilized in a total synthesis of the natural product.

Original languageEnglish (US)
Pages (from-to)587-595
Number of pages9
JournalJournal of Organic Chemistry
Volume64
Issue number2
DOIs
StatePublished - Jan 22 1999

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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