Total Synthesis of (-)-Invictolide

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 oxidativ...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 44; no. 16; pp. 2595 - 2600
Main Authors Yadav, Jhillu S., Lakshmi, K. Anantha, Reddy, N. Mallikarjuna, Prasad, Attaluri R., Al Ghamdi, Ahmad Al Khazim
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
syn-1,3-reduction
ALCOHOLS
desymmetrization strategy
DIISOPINOCAMPHEYLBORANE
oxidative lactonization
FRAGMENT
pheromones
FORMAL TOTAL-SYNTHESIS
QUEEN RECOGNITION PHEROMONE
COMPONENT
ASYMMETRIC HYDROBORATION
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Summary: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).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0032-1316561