Total Synthesis of 4-Ketoclonostachydiol

Jhillu Singh Yadav; Vijaya Vardhan; Saibal Das

doi:10.1055/s-0033-1339121

Synthesis, Table of Contents

Synthesis 2014; 46(17): 2347-2352
DOI: 10.1055/s-0033-1339121

paper

Total Synthesis of 4-Ketoclonostachydiol

Jhillu Singh Yadav*

Natural Products Chemistry Division, CSIR Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, AP, India Fax: +91(40)27160387 Email: yadavpub@iict.res.in

,

Vijaya Vardhan

Natural Products Chemistry Division, CSIR Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, AP, India Fax: +91(40)27160387 Email: yadavpub@iict.res.in

,

Saibal Das

Natural Products Chemistry Division, CSIR Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, AP, India Fax: +91(40)27160387 Email: yadavpub@iict.res.in

› Author Affiliations

Abstract

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Abstract

A facile total synthesis of nonsymmetrical 14-membered macrocyclic bis-lactone, 4-ketoclonostachydiol has been demonstrated in a convergent approach. The synthetic strategy has been unambiguously successful towards incorporating all the three stereogenic centers present in the molecule with an overall yield of 0.9%. The key synthetic step includes MacMillan hydroxylation and Grubbs ring-closing metathesis reactions to furnish the core skeleton.

Key words

marine natural product - 14-membered macrocycle - clonostachydiol - Grubbs II catalyst - total synthesis

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References

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