New Synthetic Methods Exploiting Vinyl Sulfones Discovered During the Synthesis of a Natural Product

Zhendong Jin; P. C. Vandort; P. L. Fuchs

doi:10.1080/10426509408034198

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New Synthetic Methods Exploiting Vinyl Sulfones Discovered During the Synthesis of a Natural Product

Journal article

Peer reviewed

New Synthetic Methods Exploiting Vinyl Sulfones Discovered During the Synthesis of a Natural Product

Zhendong Jin, P. C. Vandort and P. L. Fuchs

Phosphorus, sulfur, and silicon and the related elements, Vol.95(1-4), pp.1-19

10/01/1994

DOI: 10.1080/10426509408034198

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Abstract

Observations made during the synthesis of the anticancer agent homoharringtonine 37 have resulted in the development of several new synthetic methods based upon the alkylation and conjugate-addition chemistry of γ-methoxy allylsulfonyl anions. Enones, dienyl ketones, and trienyl ketones are readily constructed. Sultinium ion intermediates facilitate the sulfone to olefin transformation.

1,2-elimination of tertiary sulfone to olefin

alkylation

conjugate-addition

dienyl ketone

Intramolecular silylation of phenyl sulfone

sultinium ion

vinyl sulfone

β-substituted enone

γ-methoxy allyl sulfonyl anion

γ-methoxy vinyl sulfone

Details

Title: Subtitle: New Synthetic Methods Exploiting Vinyl Sulfones Discovered During the Synthesis of a Natural Product
Creators: Zhendong Jin - Purdue University West Lafayette
P. C. Vandort - Purdue University West Lafayette
P. L. Fuchs - Purdue University West Lafayette
Resource Type: Journal article
Publication Details: Phosphorus, sulfur, and silicon and the related elements, Vol.95(1-4), pp.1-19
Publisher: Taylor & Francis Group
DOI: 10.1080/10426509408034198
ISSN: 1042-6507
eISSN: 1563-5325
Language: English
Date published: 10/01/1994
Academic Unit: Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
Record Identifier: 9984366424802771

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