A Unified Strategy To Construct the Tetracyclic Ring of Calyciphylline A Alkaloids: Total Synthesis of Himalensine A

Jiaxin Zhong; Kuanwei Chen; Yuanyou Qiu; Haibing He; Shuanhu Gao

doi:10.1021/acs.orglett.9b01184

A Unified Strategy To Construct the Tetracyclic Ring of Calyciphylline A Alkaloids: Total Synthesis of Himalensine A

Org Lett. 2019 May 17;21(10):3741-3745. doi: 10.1021/acs.orglett.9b01184. Epub 2019 Apr 30.

Authors

Jiaxin Zhong¹, Kuanwei Chen¹, Yuanyou Qiu¹, 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 , 3663 North Zhongshan Road , Shanghai 200062 , China.
² Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , 3663 North Zhongshan Road , Shanghai 200062 , China.

PMID: 31038972
DOI: 10.1021/acs.orglett.9b01184

Abstract

The synthetic approach to the core framework of the calyciphylline A-type Daphniphyllum alkaloids and total synthesis of himalensine A were described herein. Nitrone-induced 1,3-dipolar [3 + 2] cycloaddition was applied for the construction of A/C rings along with the all-carbon quaternary center. Pd-catalyzed enolate alkenylation and ring closing metathesis (RCM) were adopted to install the B/D rings to accomplish the [6,6,5,7] core framework. Nazarov reaction was utilized to install the F ring to complete the total synthesis of himalensine A.

Publication types

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