Total Syntheses and Stereochemical Assignment of Acremolides A and B-Reference-Cited by-同舟云学术

Total Syntheses and Stereochemical Assignment of Acremolides A and B

Published:2024-07-30 Issue:15 Volume:29 Page:3599
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Xiao Yi¹,Liu Junyang¹²^ORCID,Jiang Yangyang¹,Guo Yian¹^ORCID,Ye Tao¹³^ORCID

Affiliation:

1. State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China

2. School of Pharmacy and Food Engineering, Wuyi University, Jiangmen 529020, China

3. Qian Yan (Shenzhen) Pharmatech. Ltd., Shenzhen 518172, China

Abstract

The absolute stereochemical configurations of acremolides A and B were predicted by a biochemistry-based rule and unambiguously confirmed through their total syntheses. The features of the total syntheses include sequential Krische’s Ir-catalyzed crotylation, Brown’s borane-mediated crotylation, Mitsunobu esterification reaction, and cross-metathesis reaction. The efficient total synthesis enabled clear validation of the predicted stereochemistry for acremolides A and B.

Funder

National Natural Science Foundation of China

2022 Shenzhen Sustainable Supporting Funds for Colleges and Universities

Guangdong Basic and Applied Basic Research Foundation

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/15/3599/pdf

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