Enantioselective total synthesis of (+)- and (-)-nigellamine A2

Jianwei Bian, Matthew Van Wingerden, Joseph M. Ready

Research output: Contribution to journalArticle

59 Scopus citations

Abstract

The nigellamine alkaloids are dolabellane diterpenes displaying potent lipid metabolism-promoting activity. Total synthesis of (+)- and (-)-nigellamine A2 has been accomplished. Absolute stereochemistry of synthetic nigellamine A2 was established through an intramolecular asymmetric allylic alkylation using a Pd(phosphinooxazoline) catalyst. Other notable transformations include a radical alkynylation, a diastereoselective Nozaki-Hiyama-Kishi cyclization, and a regio- and stereoselective catalytic epoxidation. On the basis of X-ray crystallographic analysis of an optically active intermediate, we have confirmed the assigned absolute stereochemistry of the natural product. Minor modifications of the synthetic sequence outlined here should provide access to the other nigellamine alkaloids.

Original languageEnglish (US)
Pages (from-to)7428-7429
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number23
DOIs
StatePublished - Jun 14 2006

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ASJC Scopus subject areas

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

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