Total Synthesis of (–)-Invictolide

Jhillu S. Yadav; K. Anantha Lakshmi; N. Mallikarjuna Reddy; Attaluri R. Prasad; Ahmad Al Khazim Al Ghamdi

doi:10.1055/s-0032-1316561

Synthesis, Table of Contents

Synthesis 2012; 44(16): 2595-2600
DOI: 10.1055/s-0032-1316561

paper

Total Synthesis of (–)-Invictolide

Authors

Jhillu S. Yadav*

Natural Product Chemistry Division, Pheromone Group, CSIR - Indian Institute of Chemical Technology, Hyderabad, 500 607, India, Fax: +91(40)27160387 Email: yadavpub@iict.res.in
K. Anantha Lakshmi

Natural Product Chemistry Division, Pheromone Group, CSIR - Indian Institute of Chemical Technology, Hyderabad, 500 607, India, Fax: +91(40)27160387 Email: yadavpub@iict.res.in
N. Mallikarjuna Reddy

Natural Product Chemistry Division, Pheromone Group, CSIR - Indian Institute of Chemical Technology, Hyderabad, 500 607, India, Fax: +91(40)27160387 Email: yadavpub@iict.res.in
Attaluri R. Prasad

Natural Product Chemistry Division, Pheromone Group, CSIR - Indian Institute of Chemical Technology, Hyderabad, 500 607, India, Fax: +91(40)27160387 Email: yadavpub@iict.res.in
Ahmad Al Khazim Al Ghamdi

Natural Product Chemistry Division, Pheromone Group, CSIR - Indian Institute of Chemical Technology, Hyderabad, 500 607, India, Fax: +91(40)27160387 Email: yadavpub@iict.res.in

Abstract

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Abstract

A convergent approach to the total synthesis of (–)-invictolide, a component of the queen recognition pheromone of Solenopsis invicta, is described. Key steps involve the desymmetrization of a bicyclic olefin with Brown’s chiral hydroboration, C–C bond formation, 1,3-syn reduction, and oxidative lactonization of a 1,3,5-triol with TEMPO/PhI(OAc)₂.

Key words

pheromones - desymmetrization strategy - syn-1,3-reduction - oxidative lactonization

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References

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