Issue 16, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol †

Adusumilli Srikrishna*a  and  Dange Vijaykumara  

* Corresponding authors

a Department of Organic Chemistry, Indian Institute of Science, Bangalore, India

Abstract

Enantiospecific total synthesis of (+)-pinguisenol 1, a sesquiterpene containing a cis-1,2,6,7-tetramethylbicyclo[4.3.0]nonane carbon framework incorporating two vicinal quaternary carbon atoms and four cis-oriented methyl groups on four contiguous carbon atoms, isolated from a liverwort, is described. The orthoester Claisen rearrangement of the allyl alcohol 9, obtained from (R)-carvone, generates the ester 12. Intramolecular cyclopropanation of the diazo ketone 13, derived from the ester 12, furnishes the tricyclic ketone 7. Degradation of the isopropenyl group followed by regioselective reductive cyclopropane ring cleavage transforms compound 7 into the hydroxy ketone 21. Wolff–Kishner reduction of the hydroxy ketone 21 followed by oxidation and Grignard reaction furnishes pinguisenol (+)-1.

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Article information

DOI
https://doi.org/10.1039/B004770H
Article type
Paper
Submitted
14 Jun 2000
Accepted
04 Jul 2000
First published
01 Aug 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2583-2589

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An enantiospecific approach to pinguisanes from (R)-carvone. Total synthesis of (+)-pinguisenol

A. Srikrishna and D. Vijaykumar, J. Chem. Soc., Perkin Trans. 1, 2000, 2583 DOI: 10.1039/B004770H

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