Studies towards the synthesis of trocheliophorolides. Issue 22 (30th May 2018)

• Record Type: Journal Article
• Authors: Khomane, Navnath B.; Meshram, Harshadas M.; Rode, Haridas B.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 22(2018)
• Page Start: 2157
• Page End: 2160
• Publication Date: 2018-05-30
• Subjects: Trocheliophorolides -- Butenolides -- Eglinton oxidative dimerization -- Cadiot-Chodkiewicz cross coupling -- Cross metathesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.04.045
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The synthesis is accomplished using commercially available ( R) -ethyl lactate. Enzymatic resolution of alcohol using amino lipase. The Eglinton oxidative coupling and Cadiot-Chodkiewicz cross coupling as key reactions. The cross metathesis using Grubbs II generation catalyst. Abstract: Total synthesis of trocheliophorolide C epimer is reported. The synthetic strategy involves generation of lactone skeleton and preparation of unsaturated side chain followed by cross-metathesis. The Eglinton oxidative coupling, Cadiot-Chodkiewicz cross-coupling and cross-metathesis are the key reactions used in the synthesis. We also attempted the synthesis of trocheliophorolide D epimer, which includes Cu catalyzed various cross-coupling reactions.