Formal synthesis of degraded sterol (+)-aplykurodinone-1

Singh, Nishant and Pulukuri, Kiran Kumar and Chakraborty, Tushar Kanti (2015) Formal synthesis of degraded sterol (+)-aplykurodinone-1. In: TETRAHEDRON, 71 (28). pp. 4608-4615.

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Abstract

The formal synthesis of aplykurodinone-1 is accomplished starting from a suitably functionalized bicyclic lactone having the requisite cis-fused ring junction with a quaternary chiral center that was assembled following a Cp2TiCl-mediated radical cyclization protocol. Our synthetic route further elaborates implementation of Grubbs ring closing metathesis (RCM), Eschenmoser-Claisen rearrangement and iodo-lactonization reactions for the synthesis of the final tricyclic precursor of the target molecule. (C) 2015 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Publication:	TETRAHEDRON
Publisher:	PERGAMON-ELSEVIER SCIENCE LTD
Additional Information:	Copy right for this article belongs to the PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Keywords:	Asymmetric Sharpless kinetic resolution; Cp2Ti(III)Cl, radical cyclization; Ring closing metathesis (RCM); Eschenmoser-Claisen rearrangement; Iodolactonization
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	27 Jul 2015 12:11
Last Modified:	27 Jul 2015 12:11
URI:	http://eprints.iisc.ac.in/id/eprint/51909

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