Asymmetric Total Synthesis of PD-116740

Chaoying Zheng; Tao Xie; Haibing He; Shuanhu Gao

doi:10.1021/acs.orglett.0c03990

Asymmetric Total Synthesis of PD-116740

Org Lett. 2021 Jan 15;23(2):469-473. doi: 10.1021/acs.orglett.0c03990. Epub 2021 Jan 5.

Authors

Chaoying Zheng¹, Tao Xie¹, Haibing He², Shuanhu Gao^{1

2}

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663North Zhongshan Road, Shanghai 200062, China.
² Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663N Zhongshan Road, Shanghai 200062, China.

PMID: 33400535
DOI: 10.1021/acs.orglett.0c03990

Abstract

A new approach was developed to achieve the asymmetric total synthesis of (+)-PD-116740, an angucyclinone from the actinomycete isolate (WP 4669). A sequence of asymmetric dihydroxylation followed by oxidative cyclization was applied to stereoselectively construct the core trans-9,10-dihydrophenanthrene-9,10-diol B-C-D ring. A new Cu salt Cu(OH)OTf·NMI₂ was found to be the best oxidant to induce the oxidative coupling and phenol oxidation.

Publication types

Research Support, Non-U.S. Gov't