Stereoselective synthesis of (10S, 12S)-10-hydroxy-12-methyl-1-oxacyclododecane-2, 5-dione via Prins cyclization

Yadav, J. S. ; Thrimurtulu, N. ; Venkatesh, M. ; Raghavendra Rao, K. V. ; Prasad, A. R. ; Subba Reddy, B. V. (2010) Stereoselective synthesis of (10S, 12S)-10-hydroxy-12-methyl-1-oxacyclododecane-2, 5-dione via Prins cyclization Synthesis, 1 . pp. 73-78. ISSN 0039-7881

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Official URL: https://www.thieme-connect.com/ejournals/abstract/...

Related URL: http://dx.doi.org/10.1055/s-0029-1217107

Abstract

The total synthesis of (10S,12S)-10-hydroxy-12-methyl-1-oxacyclododecane-2,5-dione is described proving the versatility of the Prins cyclization in natural products synthesis. The approach is convergent and highly stereoselective. Prins cyclization, esterification, ring-closing metathesis and oxidation reactions are utilized as key steps in the synthesis of this macrolactone.

Item Type:Article
Source:Copyright of this article belongs to Thieme Medical Publishers.
Keywords:Prins Cyclization; Esterification; Ring-closing Metathesis; Macrolactone
ID Code:63169
Deposited On:28 Sep 2011 03:46
Last Modified:28 Sep 2011 03:46

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