Formal total synthesis of (−)-spongidepsin

Chandrasekhar, S. ; Yaragorla, S. R. ; Sreelakshmi, L. ; Raji Reddy, Ch. (2008) Formal total synthesis of (−)-spongidepsin Tetrahedron, 64 (22). pp. 5174-5183. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tet.2008.03.041

Abstract

The formal total synthesis of (−)-spongidepsin is described. Three fragments I, II, and III were first prepared from readily available starting materials and then assembled to the target compound. The key steps involved in the synthesis are asymmetric α-hydroxylation, Ender's alkylation, and ring-closing metathesis reactions. An alternative route for the fragment II is also achieved involving Sharpless asymmetric epoxidation and Gilman's alkylation as key reactions.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Spongidepsin; D-proline; Enders Auxiliary; Sharpless Asymmetric Epoxidation; Gilman's Alkylation; RCM
ID Code:62361
Deposited On:22 Sep 2011 03:34
Last Modified:22 Sep 2011 03:34

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