Synthetic Progress toward Azadirachtins. 2. Enantio- and Diastereoselective Synthesis of the Right-Wing Fragment of 11-epi-Azadirachtin I

Ceheng Tan; Wei Chen; Xinpeng Mu; Qi Chen; Jianxian Gong; Tuoping Luo; Zhen Yang

doi:10.1021/acs.orglett.5b00831

Synthetic Progress toward Azadirachtins. 2. Enantio- and Diastereoselective Synthesis of the Right-Wing Fragment of 11-epi-Azadirachtin I

Org Lett. 2015 May 15;17(10):2338-41. doi: 10.1021/acs.orglett.5b00831. Epub 2015 Apr 28.

Authors

Ceheng Tan¹, Wei Chen¹, Xinpeng Mu¹, Qi Chen¹, Jianxian Gong¹, Tuoping Luo², Zhen Yang^{1

2

3}

Affiliations

¹ †Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
² ‡Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS) and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.
³ §Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.

PMID: 25919947
DOI: 10.1021/acs.orglett.5b00831

Abstract

A stereoselective three-component coupling reaction of allylzinc bromide, silyl glyoxylate, and a β-lactone has been developed. This has been successfully applied to the enantio- and diastereoselective synthesis of the fully functionalized furopyran moiety of azadirachtins.

Publication types

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

MeSH terms

Glyoxylates / chemistry*
Lactones / chemistry*
Limonins / chemical synthesis*
Limonins / chemistry
Molecular Structure
Stereoisomerism
Zinc Compounds / chemistry*

Substances

Glyoxylates
Lactones
Limonins
Zinc Compounds
glyoxylic acid
azadirachtin