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Article

Total Syntheses and Stereochemical Assignment of Acremolides A and B

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
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2024, 29(15), 3599; https://doi.org/10.3390/molecules29153599 (registering DOI)
Submission received: 25 June 2024 / Revised: 24 July 2024 / Accepted: 26 July 2024 / Published: 30 July 2024
(This article belongs to the Special Issue Bioactive Molecules: Isolation, Synthesis, Analysis, and Application)

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.
Keywords: total syntheses; natural products; asymmetric crotylation; acremolide total syntheses; natural products; asymmetric crotylation; acremolide

Share and Cite

MDPI and ACS Style

Xiao, Y.; Liu, J.; Jiang, Y.; Guo, Y.; Ye, T. Total Syntheses and Stereochemical Assignment of Acremolides A and B. Molecules 2024, 29, 3599. https://doi.org/10.3390/molecules29153599

AMA Style

Xiao Y, Liu J, Jiang Y, Guo Y, Ye T. Total Syntheses and Stereochemical Assignment of Acremolides A and B. Molecules. 2024; 29(15):3599. https://doi.org/10.3390/molecules29153599

Chicago/Turabian Style

Xiao, Yi, Junyang Liu, Yangyang Jiang, Yian Guo, and Tao Ye. 2024. "Total Syntheses and Stereochemical Assignment of Acremolides A and B" Molecules 29, no. 15: 3599. https://doi.org/10.3390/molecules29153599

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