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Asymmetric Total Synthesis of Propindilactone G

Authors :
Yuefan Wang
Yuan-He Li
Ling-Min Xu
Lin You
Bo Zhang
Jia-Jun Zhang
Jiahua Chen
Xin-Ting Liang
Shouliang Yang
Qi Su
Zhen Yang
Source :
Journal of the American Chemical Society. 137:10120-10123
Publication Year :
2015
Publisher :
American Chemical Society (ACS), 2015.

Abstract

A concise total synthesis of (+)-propindilactone G, a nortriterpenoid isolated from the stems of Schisandra propinqua var. propinqua, has been achieved for the first time. The key steps of the synthesis include an asymmetric Diels-Alder reaction, a Pauson-Khand reaction, a Pd-catalyzed reductive hydrogenolysis reaction, and an oxidative heterocoupling reaction. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised.

Details

ISSN :
15205126 and 00027863
Volume :
137
Database :
OpenAIRE
Journal :
Journal of the American Chemical Society
Accession number :
edsair.doi.dedup.....a94feefc806c8b4fa5716bf5591ccf70