Enantioselective double Michael addition/cyclization with an oxygen- centered nucleophile as the first step in a concise synthesis of natural (+)- asteriscanolide

Leo A. Paquette, Jinsung Tae, Mark P. Arrington, Aladin H. Sadoun

Research output: Contribution to journalArticle

91 Citations (Scopus)

Abstract

The total synthesis of (+)-asteriscanolide (1) starting from 2-bromo- 4,4-dimethylcyclopentenone has been accomplished. The synthetic route features two key steps. The first step is an unprecedented Michael-Michael reaction sequence that involves a heteronucleophile and proceeds with complete asymmetric induction. The two five-membered rings of the target molecule are thereby generated enantioselectively in a single laboratory step. The second step is based on utilization of ring-closing metathesis to provide an eight-membered ring in which a conjugated 1,3-diene unit resides. Other features of the synthetic stratagem involve the utilization of singlet oxygen in a regiocontrolled ene reaction, the fully stereocontrolled hydrogenation of a dienone, and a chemoselective ruthenium tetraoxide oxidation.

Original languageEnglish
Pages (from-to)2742-2748
Number of pages7
JournalJournal of the American Chemical Society
Volume122
Issue number12
DOIs
Publication statusPublished - 2000 Mar 29

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Enantioselective double Michael addition/cyclization with an oxygen- centered nucleophile as the first step in a concise synthesis of natural (+)- asteriscanolide'. Together they form a unique fingerprint.

  • Cite this