Catalytic Asymmetric Total Syntheses of (+)- and (−)-ar-Elvirol Methyl Ether

Debabrata Mondal; Dhruvilkumar Sureshkumar Patel; Vishnumaya Bisai

doi:10.1055/a-2675-4038

Synlett, Table of Contents

Synlett
DOI: 10.1055/a-2675-4038

Letter

Published as part of the Special Issue dedicated to Prof. S. Chandrasekaran on his 80th birthday

Catalytic Asymmetric Total Syntheses of (+)- and (−)-ar-Elvirol Methyl Ether

Authors

Debabrata Mondal

¹Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, West Bengal, India (Ringgold ID: RIN548707)
Dhruvilkumar Sureshkumar Patel

²Department of Chemistry, School of Sciences, Indrashil University, Rajpur, Gujarat, India (Ringgold ID: RIN597127)
Vishnumaya Bisai

²Department of Chemistry, School of Sciences, Indrashil University, Rajpur, Gujarat, India (Ringgold ID: RIN597127)

Abstract

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Dedication

This paper is dedicated respectfully to Prof. S. Chandrasekaran, Department of Organic Chemistry, IISc Bangalore, India, on the occasion of his 80th birthday.

Abstract

A catalytic asymmetric approach to either of the enantiomers of naturally occurring sesquiterpenes, i.e., (+)-ar-elvirol (1a) and (−)-ar-elvirol (ent-1a), has been achieved via a reductive transposition of a tertiary alcohol following a key allylic diazene arrangement (ADR) from an advanced enantioenriched tertiary allyl alcohol. The ADR proceeds via the reductive transposition of olefin under the Mitsunobu reaction with o-nitro benzene sulfonyl hydrazide followed by the decomposition of the sulfonyl hydrazide adduct. This approach has been utilized for the total syntheses of bisabolene sesquiterpenoids, (+)-ar-elvirol methyl ether (1b) and (−)-ar-elvirol methyl ether (ent-1b).

Keywords

Allylic diazene rearrangement (ADR) - Asymmetric conjugate addition - Aromatic bisabolanes - E-Ethyl crotonate - Boronic acid - (+)-ar-Elvirol (1a) - (+)-ar-Elvirol methyl ether (1b)

Full Text

References

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