Synthesis of the tetrahydrofuran unit of varitriol and γ-butyrolactones from 5-oxabicyclo[2.1.1]hexane derivative via oxidative cleavage reactions

Mahadevegowda, S H and Khan, Faiz Ahmed (2014) Synthesis of the tetrahydrofuran unit of varitriol and γ-butyrolactones from 5-oxabicyclo[2.1.1]hexane derivative via oxidative cleavage reactions. Tetrahedron Letters, 55 (14). pp. 2266-2269. ISSN 0040-4039

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Abstract

A formal synthesis of marine-derived antitumor natural product varitriol from a 5-oxabicyclo[2.1.1]hexane derivative is described. A tetrahydrofuran unit of varitriol embedded with four contiguous stereocenters was synthesized with an overall yield of 10.2% in 11 steps from an oxa-bicyclic system. An unprecedented oxidative cleavage reaction involving scissoring of two Csingle bondC bonds at oxa-quaternary carbon of THFs leading to γ-butyrolactones was reported and a plausible mechanism has been proposed.

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IITH Creators:	IITH Creators ORCiD Khan, Faiz Ahmed UNSPECIFIED
Item Type:	Article
Uncontrolled Keywords:	Antitumor natural product; Deacetoxylation; Pyridinium dichromate; Bis-oxidative cleavage
Subjects:	Chemistry
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	05 Jan 2016 08:29
Last Modified:	21 Sep 2017 06:55
URI:	http://raiithold.iith.ac.in/id/eprint/2096
Publisher URL:	https://doi.org/10.1016/j.tetlet.2014.02.082
OA policy:	http://www.sherpa.ac.uk/romeo/issn/0040-4039/
Related URLs:	Google Scholar

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