Studies toward the total synthesis of Cytospolide E. Issue 48 (2nd December 2015)

• Record Type: Journal Article
• Authors: Vadhadiya, Paresh M.; Rout, Jeetendra K.; Ramana, C.V.
• Is Part Of: Tetrahedron. Volume 71:Issue 48(2015)
• Page Start: 9088
• Page End: 9094
• Publication Date: 2015-12-02
• Subjects: Nonenolide -- Yamaguchi esterification -- Ring closing metathesis -- Shiina lactonization -- 20-Membered macrodiolide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.10.018
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: In this manuscript, we describe various approaches that we have examined towards the total synthesis of Cytospolide E. We initially attempted the RCM approach employing first and second generation Grubbs and Grubbs–Hoyeda catalysts resulting in the exclusive synthesis of the Z -isomer of Cytospolide E. With the Fürstner catalyst, the dimerization involving the less hindered olefin was the exclusive event. Alternative approach documented is a successful cross-metathesis leading to a seco -acid with the requisite E -configuration and undesired macrodiolide formation during the attempted Shiina's lactonization. Graphical abstract: