Synthesis 2016; 48(06): 917-923
DOI: 10.1055/s-0035-1561319
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the C1–C13 Fragment of Mandelalide A

Sudhakar Athe
CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500007, India   Email: subhash@iict.res.in
,
Subhash Ghosh*
CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500007, India   Email: subhash@iict.res.in
› Author Affiliations
Further Information

Publication History

Received: 06 November 2015

Accepted after revision: 15 December 2015

Publication Date:
11 January 2016 (online)


Abstract

This communication describes the synthesis of the fully functionalized C1 to C13 segment (southern part) of highly potent cytotoxic marine natural product mandelalide A. Pd-catalyzed oxa-­Michael cyclization followed by stereoselective reduction of the C7-ketone were carried out to construct the tetrahydropyran unit with required stereochemistry. The α,β-unsaturated ester moiety was constructed via cross-metathesis and the vinyl iodide was installed through modified Takai olefination.

Supporting Information

 
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