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An Approach to seco-Prezizaane Sesquiterpenoids: Enantioselective Total Synthesis of (+)-1S-Minwanenone

Mehta, Goverdhan and Shinde, Harish M (2012) An Approach to seco-Prezizaane Sesquiterpenoids: Enantioselective Total Synthesis of (+)-1S-Minwanenone. In: JOURNAL OF ORGANIC CHEMISTRY, 77 (18). pp. 8056-8070.

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Official URL: http://dx.doi.org/10.1021/jo301258g

Abstract

A strategy of general applicability toward seco-prezizaane sesquiterpenes, from a chiral, tricyclic synthon, readily available via an enzymatic resolution step from the Diels-Alder adduct of cyclopentadiene and p-benzoquinone, has been devised. Our approach enables harnessing of the stereochemical proclivities of the norbornyl system to install the desired stereochemistry at the key stereogenic centers. Recourse to an interesting stratagem to realign a stereochemical divergence into stereoreconvergence forms the cornerstone of our successful approach. The first total synthesis of (+)-1S-minwanenone, a prototypical member of seco-prezizaane subclass, has been accomplished.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to the AMER CHEMICAL SOC, WASHINGTON,
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Francis Jayakanth
Date Deposited: 13 Dec 2012 05:23
Last Modified: 13 Dec 2012 05:23
URI: http://eprints.iisc.ac.in/id/eprint/45500

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