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A Vicarious One-Pot Transformation of a Fluorocyclitol to a Polycyclitol: Observation of a Formal 4-Fold Axial-Equatorial Epimerization on a Conformationally Locked Scaffold

Mehta, Goverdhan and Sen, Saikat (2010) A Vicarious One-Pot Transformation of a Fluorocyclitol to a Polycyclitol: Observation of a Formal 4-Fold Axial-Equatorial Epimerization on a Conformationally Locked Scaffold. In: Journal of Organic Chemistry, 75 (23). pp. 8287-8290.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo101660x

Abstract

A conformationally locked fluoropentol undergoes an interesting transformation to (trans,anti,trans,anti,trans)-perhydro-2,3,4a,6,7,8a-naphthalenehexol essentially under conditions of base-induced transesterification. The proposed rationale for the observed metamorphosis involves a nucleophilic displacement of fluoride, and subsequent stereo- and regioselective anti-Furst-Plattner-type ring-opening of the epoxide thus formed.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 27 Dec 2010 07:16
Last Modified: 27 Dec 2010 07:16
URI: http://eprints.iisc.ernet.in/id/eprint/34600

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