Total Synthesis of Sordaricin

Lewis N. Mander* and Regan J. Thomson
Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia
J. Org. Chem., 2005, 70 (5), pp 1654–1670
DOI: 10.1021/jo048199b
Publication Date (Web): January 25, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mander@rsc.anu.edu.au

Abstract

Abstract Image

An enantioconvergent total synthesis of sordaricin (3), the diterpene aglycon of an important class of antifungal compounds, is described. Two approaches were explored, the first of which utilized a possible biogenetic intramolecular [4 + 2] cycloaddition to form the complete carbon skeleton of the target molecule as a single regioisomer 30. A second approach employed a tandem cycloreversion/intramolecular [4 + 2] cycloaddition process to afford not only the desired product 30 but also significant quantities of the undesired regioisomer iso-30. An investigation into the reasons for the difference in regioselectivity between these two reactions revealed the intervention of a cycloreversion/cycloaddition pathway at elevated temperatures leading to the formation of iso-30. Experimental evidence supports the hypothesis that iso-30 is the more thermodynamically stable of the two regioisomers.

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History

  • Published In Issue March 04, 2005
  • Received October 12, 2004

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