Total Synthesis of the Z-Isomers of the Proposed and Revised Structures of Aspergillide B via an Iodocyclization and Ring-Closing Metathesis Strategy

Tapas R. Pradhan; Pragna P. Das; Debendra K. Mohapatra

doi:10.1055/s-0033-1340853

Synthesis, Table of Contents

Synthesis 2014; 46(09): 1177-1184
DOI: 10.1055/s-0033-1340853

paper

Total Synthesis of the Z-Isomers of the Proposed and Revised Structures of Aspergillide B via an Iodocyclization and Ring-Closing Metathesis Strategy

Authors

Tapas R. Pradhan

Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India Fax: +91(40)27160512 Email: mohapatra@iict.res.in
Pragna P. Das

Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India Fax: +91(40)27160512 Email: mohapatra@iict.res.in
Debendra K. Mohapatra*

Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India Fax: +91(40)27160512 Email: mohapatra@iict.res.in

Abstract

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Abstract

The synthesis of Z-isomers of both the proposed and revised structures of aspergillide B is described. A divergent route is employed that involves kinetically controlled ring-closing metathesis for the construction of a 14-membered macrocyclic ring, ester formation under Yamaguchi conditions, a Wacker-type oxidative cyclization for creation of the C4 stereogenic center and a previously reported diastereoselective isomerization–iodocyclization strategy for the construction of the 2,6-trans-disubstituted tetrahydropyran subunit.

Key words

aspergillides - ring-closing metathesis - Yamaguchi esterification - Wacker-type oxidation - iodocyclization - cytotoxic activity

Full Text

References

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Supplementary Material

Supporting Information (PDF)