Total Synthesis of Nannocystin A

Zhantao Yang; Xiaolong Xu; Chun-Hua Yang; Yunfeng Tian; Xinyi Chen; Lihui Lian; Wenwei Pan; Xuncheng Su; Weicheng Zhang; Yue Chen

doi:10.1021/acs.orglett.6b02729

Total Synthesis of Nannocystin A

Org Lett. 2016 Nov 4;18(21):5768-5770. doi: 10.1021/acs.orglett.6b02729. Epub 2016 Oct 13.

Authors

Zhantao Yang^{1

2}, Xiaolong Xu¹, Chun-Hua Yang^{1

2}, Yunfeng Tian¹, Xinyi Chen¹, Lihui Lian¹, Wenwei Pan¹, Xuncheng Su³, Weicheng Zhang¹, Yue Chen¹

Affiliations

¹ State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University , Tianjin 300353, P. R. China.
² College of Chemistry and Chemical Engineering, Anyang Normal University , Anyang 455000, P. R. China.
³ State Key Laboratory of Elemento-organic Chemistry, Nankai University , Tianjin 300071, P. R. China.

PMID: 27736074
DOI: 10.1021/acs.orglett.6b02729

Abstract

Nannocystin A is a 21-membered cyclodepsipeptide showing remarkable anticancer properties. Described is the total synthesis of nannocystin A, which features an asymmetric vinylogous Mukaiyama aldol reaction for efficient assembly of the penultimate open-chain precursor and a pivotal intramolecular Heck cross-coupling for the final macrocyclization.

Publication types

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

MeSH terms

Cyclization
Macrocyclic Compounds / chemical synthesis*
Macrocyclic Compounds / chemistry
Molecular Conformation

Substances

Macrocyclic Compounds
nannocystin A