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Synthesis 2014; 46(21): 2927-2936
DOI: 10.1055/s-0034-1379003
paper
© Georg Thieme Verlag Stuttgart · New York

Exploring a Ring-Closing Metathesis Approach to the Archazolid Macrocycle

Authors

  • Brianne R. King

    Department of Chemistry, Western Washington University, Bellingham, WA 98225, USA   Fax: +1(360)6502826   Email: oneil@chem.wwu.edu

  • Steven M. Swick

    Department of Chemistry, Western Washington University, Bellingham, WA 98225, USA   Fax: +1(360)6502826   Email: oneil@chem.wwu.edu

  • Sara L. Schaefer

    Department of Chemistry, Western Washington University, Bellingham, WA 98225, USA   Fax: +1(360)6502826   Email: oneil@chem.wwu.edu

  • Jamie R. Welch

    Department of Chemistry, Western Washington University, Bellingham, WA 98225, USA   Fax: +1(360)6502826   Email: oneil@chem.wwu.edu

  • Emily F. Hunter

    Department of Chemistry, Western Washington University, Bellingham, WA 98225, USA   Fax: +1(360)6502826   Email: oneil@chem.wwu.edu

  • Gregory W. O’Neil*

    Department of Chemistry, Western Washington University, Bellingham, WA 98225, USA   Fax: +1(360)6502826   Email: oneil@chem.wwu.edu
Further Information

Publication History

Received: 17 June 2014

Accepted after revision: 28 July 2014

Publication Date:
15 August 2014 (online)

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Graphical Abstract

Abstract

The synthesis of a new ‘eastern domain’ of a proposed dihydroarchazolid analogue is described along with initial results from attempted macrocyclization by ring-closing metathesis. This work has revealed a competing backbiting process that may be preventable by alcohol functionalization and installation of a metathesis relay.

Key words

total synthesis - natural products - olefin metathesis - relay ring-closing metathesis

Supporting Information