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Application of Cp2TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes

Khan, Hina P A and Das, Dipendu and Chakraborty, Tushar Kanti (2018) Application of Cp2TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes. In: JOURNAL OF ORGANIC CHEMISTRY, 83 (11). pp. 6086-6092.

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Official URL: https://dx.doi.org/10.1021/acs.joc.8b00752

Abstract

An expedient approach toward the unified total syntheses of (+)-iridomyrmecin, (-)-isoiridomyrmecin, (+)-7-epiboschnialactone, (+)-teucriumlactone, and (-)-dolichodial in chirally pure forms starting from readily available (+)-beta-citronellene is delineated combining step economy and simplicity. Highlights include a Ti(III)-mediated reductive epoxide opening-cydization for the construction of the core cyclopentac]pyran skeleton of the iridoid lactones with complete diastereoselectivity for the newly created bridgehead stereogenic centers. Subsequent transformations facilitate a short access to (+)-teucriumlactone and (-)-dolichodial and formal access to potentially other iridoids.

Item Type: Journal Article
Additional Information: Copy right of this article belong to AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 26 Jun 2018 14:20
Last Modified: 26 Jun 2018 14:20
URI: http://eprints.iisc.ac.in/id/eprint/60086

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