Efficient asymmetric total syntheses of cryptocarya triacetate, cryptocaryolone, and cryptocaryolone diacetate

Xiaolei Wang; Wenkuan Wang; Huaiji Zheng; Yingpeng Su; Tuo Jiang; Yongping He; Xuegong She

doi:10.1021/ol901024t

Efficient asymmetric total syntheses of cryptocarya triacetate, cryptocaryolone, and cryptocaryolone diacetate

Org Lett. 2009 Jul 16;11(14):3136-8. doi: 10.1021/ol901024t.

Authors

Xiaolei Wang¹, Wenkuan Wang, Huaiji Zheng, Yingpeng Su, Tuo Jiang, Yongping He, Xuegong She

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.

PMID: 19537772
DOI: 10.1021/ol901024t

Abstract

Concise and efficient asymmetric total syntheses of three substituted alpha-pyrone-type natural products have been accomplished via 7-9 steps from 5b in high overall yields, which involve linchpin coupling, ring-closing metathesis, and a tandem sequence of deacetylation and intramolecular oxa-Michael addition as the key steps.

Publication types

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

MeSH terms

Biological Products / chemical synthesis*
Biological Products / chemistry
Catalysis
Molecular Structure
Plants, Medicinal / chemistry
Pyrones / chemical synthesis*
Pyrones / chemistry

Substances

Biological Products
Pyrones
cryptocarya triacetate
cryptocaryolone
cryptocaryolone diacetate