First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening

Citation data:

Tetrahedron: Asymmetry, ISSN: 0957-4166, Vol: 28, Issue: 2, Page: 246-249

Publication Year:
2017
Usage 5
Abstract Views 5
Captures 10
Readers 9
Exports-Saves 1
Social Media 147
Shares, Likes & Comments 147
Citations 5
Citation Indexes 5
DOI:
10.1016/j.tetasy.2017.01.005
Author(s):
Perla Ramesh; Yarram Narasimha Reddy; Thatikonda Narendar Reddy; Navuluri Srinivasu
Publisher(s):
Elsevier BV
Tags:
Chemical Engineering; Chemistry
article description
The first protecting group-free total syntheses of the highly potent antitumor chlorinated styryllactone secondary metabolites 8-chlorogoniodiol, parvistone A, and one analogue 8- epi -parvistone A, have been accomplished from commercially available trans -cinnamaldehyde in five steps with high overall yields. The chlorine-bearing stereogenic center of these silent secondary metabolites was introduced via a bioinspired late-stage regioselective epoxide ring-opening strategy. Maruoka asymmetric allylation, acrylation, ring-closing metathesis and asymmetric epoxidation, greatly facilitate the synthesis of the key intermediates goniothalamin oxide and (6 S,7 S,8 S )-isogoniothalamin oxide.