Full Paper

Studies toward the Synthesis of (−)-Zampanolide: Preparation of the Macrocyclic Core

  1. Dawn M. Troast,
  2. Jiayi Yuan,
  3. John A. Porco Jr.

Article first published online: 9 JUL 2008

DOI: 10.1002/adsc.200800247

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 350, Issue 11-12, pages 1701–1711, August 4, 2008

Additional Information

How to Cite

Troast, Dawn M., Yuan, J. and Porco, John A. (2008), Studies toward the Synthesis of (−)-Zampanolide: Preparation of the Macrocyclic Core. Adv. Synth. Catal., 350: 1701–1711. doi: 10.1002/adsc.200800247

Author Information

  1. Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1)-617-358-2847

Publication History

  1. Issue published online: 31 JUL 2008
  2. Article first published online: 9 JUL 2008
  3. Manuscript Received: 24 APR 2008

Funded by

  • National Institutes of Health. Grant Number: RO1 GM-62842
  • Bristol-Myers Squibb
  • Novartis
  • Wyeth
  • Merck

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Keywords:

  • allylsilanes;
  • macrolide;
  • exo-methylene pyrans;
  • sp2-sp3 coupling;
  • Stille reaction;
  • zampanolide

Abstract

Studies towards the synthesis of the macrocyclic core of (−)-zampanolide are reported. The synthetic approach features a one-pot reduction/vinylogous aldol reaction for construction of the C-15–C-20 fragment, an intramolecular silyl-modified Sakurai (ISMS) reaction for construction of the 2,6-cis-disubstituted exo-methylene pyran subunit, and use of an sp2-sp3 Stille reaction for macrocyclization.

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