Scalable Total Synthesis of (-)-Vinigrol

Xuerong Yu; Lianghong Xiao; Zechun Wang; Tuoping Luo

doi:10.1021/jacs.9b00621

Scalable Total Synthesis of (-)-Vinigrol

J Am Chem Soc. 2019 Feb 27;141(8):3440-3443. doi: 10.1021/jacs.9b00621. Epub 2019 Feb 18.

Authors

Xuerong Yu¹, Lianghong Xiao¹, Zechun Wang¹, Tuoping Luo^{1

2}

Affiliations

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
² Peking-Tsinghua Center for Life Sciences, Academy for Advanced Interdisciplinary Studies , Peking University , Beijing 100871 , China.

PMID: 30767520
DOI: 10.1021/jacs.9b00621

Abstract

Vinigrol is a structurally and stereochemically complex natural product that displays various potent pharmacological activities, including the capability to modulate TNF-α. A new and efficient synthetic route toward this natural product has been developed to complete the asymmetric synthesis of (-)-vinigrol and provide over 600 mg of material, manifesting the power of macrocyclic stereocontrol and transannular Diels-Alder reaction.

Publication types

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