Stereoselective synthesis of functionalized allenes from tartaric acid

Shruthi, KS and Singh, P and Prasad, KR (2020) Stereoselective synthesis of functionalized allenes from tartaric acid. In: Tetrahedron .

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Abstract

Desymmetrization of the C2-symmetric bis-dimethylamide derived from tartaric acid by controlled addition of alkynyl lithium reagents furnished the mono alkynyl ketones which on reduction produced the corresponding propargyl alcohols with good diastereoselectivity. The propargyl alcohols were transformed to allenes using Claisen rearrangement. The formed allenes serve as a precursor for the synthesis of one of the THP units of the natural product sorangicin and for the synthesis of the polyhydroxy unit present in natural product anamarine. © 2020 Elsevier Ltd

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier Ltd
Additional Information:	The copyright of this article belongs to Elsevier Ltd
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	15 Mar 2021 09:22
Last Modified:	15 Mar 2021 09:22
URI:	http://eprints.iisc.ac.in/id/eprint/67457

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