Determination of the Absolute Configuration of Gliomasolide D through Total Syntheses of the C-17 Epimers

Seetharamsingh, B. ; Ganesh, Routholla ; Reddy, D. Srinivasa (2017) Determination of the Absolute Configuration of Gliomasolide D through Total Syntheses of the C-17 Epimers Journal of Natural Products, 80 (2). pp. 560-564. ISSN 0163-3864

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Official URL: http://doi.org/10.1021/acs.jnatprod.6b00926

Related URL: http://dx.doi.org/10.1021/acs.jnatprod.6b00926

Abstract

The absolute configuration at C-17, the carbon bearing the distal hydroxy group of the 14-membered natural product gliomasolide D, was assigned as R by comparison of 13C NMR shifts and specific rotation values of the epimers at C-17. The first total synthesis of gliomasolide D along with its C-17 epimer, regioselective macrocyclization (18 membered vs 14 membered), and regioselective Wacker oxidation are highlights of the present work.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:121928
Deposited On:23 Jul 2021 08:22
Last Modified:23 Jul 2021 08:22

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