Asymmetric total synthesis and structural elucidation of NFAT-68

Lin Wang; Yumeng Xi; Shouliang Yang; Rong Zhu; Yufan Liang; Jiahua Chen; Zhen Yang

doi:10.1021/ol102574d

Asymmetric total synthesis and structural elucidation of NFAT-68

Org Lett. 2011 Jan 7;13(1):74-7. doi: 10.1021/ol102574d. Epub 2010 Dec 1.

Authors

Lin Wang¹, Yumeng Xi, Shouliang Yang, Rong Zhu, Yufan Liang, Jiahua Chen, Zhen Yang

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 10087, China.

PMID: 21121639
DOI: 10.1021/ol102574d

Abstract

Total synthesis of NFAT-68 (7) has been achieved and its relative stereochemistry has been determined. A key step thereof is the utilization of the chelation-controlled vinylogous Mukaiyama aldol reaction (VMAR) to stereoselectively synthesize the syn-aldol product 8. This developed chemistry is anticipated to have wider application in total syntheses of many other natural products.

Publication types

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

MeSH terms

Crystallography, X-Ray
Hydroquinones / chemical synthesis*
Models, Molecular
Molecular Structure
Stereoisomerism

Substances

Hydroquinones
NFAT 68