Asymmetric Total Synthesis of (+)-Mannolide C

Qiaoqiao Ao; Hai-Jun Zhang; Jinbin Zheng; Xiaoming Chen; Hongbin Zhai

doi:10.1002/anie.202107954

Asymmetric Total Synthesis of (+)-Mannolide C

Angew Chem Int Ed Engl. 2021 Sep 20;60(39):21267-21271. doi: 10.1002/anie.202107954. Epub 2021 Aug 20.

Authors

Qiaoqiao Ao¹, Hai-Jun Zhang¹, Jinbin Zheng¹, Xiaoming Chen², Hongbin Zhai^{1

3

4}

Affiliations

¹ The State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Nano-Micro Materials Research, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen, 518055, China.
² State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China.
³ Institute of Marine Biomedicine, Shenzhen Polytechnic, Shenzhen, 518055, China.
⁴ Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300071, China.

PMID: 34312950
DOI: 10.1002/anie.202107954

Abstract

(+)-Mannolide C is a complex hexacyclic C₂₀ cephalotane-type diterpenoid featuring a highly strained 7/6/6/5 tetracyclic core containing eight consecutive stereocenters and two bridging lactones. The first asymmetric total synthesis of (+)-mannolide C has been accomplished by lipase-mediated resolution, Ru-complex-catalyzed double ring-closing metathesis (RCM) reactions, Ni^II -catalyzed diastereoselective Michael addition, and Mn^III -catalyzed allylic oxidation as the key transformations.

Keywords: (+)-mannolide C; cephalotaxus diterpenoids; ring-closing metathesis; total synthesis.

Publication types

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