Short Communication

Studies on the Synthesis of Schisandraceae Natural Products: Exploring a Cyclopropylcarbinol Ring Expansion Strategy

  1. Derek Fischer,
  2. Emmanuel A. Theodorakis

Article first published online: 31 MAY 2007

DOI: 10.1002/ejoc.200700336

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2007, Issue 25, pages 4193–4196, September 2007

Additional Information

How to Cite

Fischer, D. and Theodorakis, E. A. (2007), Studies on the Synthesis of Schisandraceae Natural Products: Exploring a Cyclopropylcarbinol Ring Expansion Strategy. Eur. J. Org. Chem., 2007: 4193–4196. doi: 10.1002/ejoc.200700336

Author Information

  1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA, Fax: +1-858-822-0386

Publication History

  1. Issue published online: 10 AUG 2007
  2. Article first published online: 31 MAY 2007
  3. Manuscript Received: 17 APR 2007

Funded by

  • Cancer Research Coordinating Committee. Grant Number: 6-446228-37607

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (118K)

Keywords:

  • Synthesis design;
  • Cyclopropanation;
  • Synthetic methods;
  • Baeyer–Villiger oxidation;
  • Ring expansion

Abstract

Acid mediated cyclopropylcarbinol ring expansion has been shown to be a viable method for the construction of the AB ring framework of lancifodilactone F and related terpenoids of the Schisandraceae family of natural products. We found that this rearrangement proceeds with good stereochemical control based on inversion of the C10 cyclopropyl center. Our studies indicate that the cis-decalin motif of 31 could be used as a key synthetic precursor of certain Schisandraceae metabolites.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

View Full Article with Supporting Information (HTML) Get PDF (118K)