Formal synthesis of Cladospolide C & epi-Cladospolide C using R-(+)-γ-valerolactone as a chiral synthon. Issue 19 (10th May 2019)

• Record Type: Journal Article
• Authors: Datrika, Rajender; Kallam, Srinivasa Reddy; Vidavalur, Siddaiah; Rajana, Nagaraju; Pratap, T.V.
• Is Part Of: Tetrahedron. Volume 75:Issue 19(2019)
• Page Start: 2824
• Page End: 2831
• Publication Date: 2019-05-10
• Subjects: Cladospolide -- Gamma valerolactone -- Wittig reaction -- Yamaguchi lactonization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.04.001
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The formal synthesis of Cladospolide-C and its analog is achieved by using enantiopure ( R )-γ–valerolactone10 . The significant points of this synthesis are the stereoselective dihydroxylation of α, β -unsaturated ester16 using Sharpless protocol, Wittig olefination of γ –valerolactol6 with triphenylphosphonium iodide salt7, one pot selective oxidation of22 and subsequent C2-homologation with good E / Z ratio. Graphical abstract: Image 1