Total Synthesis of (-)-Enigmazole A

Yanran Ai; Mariya V Kozytska; Yike Zou; Anton S Khartulyari; Amos B Smith 3rd

doi:10.1021/jacs.5b11540

Total Synthesis of (-)-Enigmazole A

J Am Chem Soc. 2015 Dec 16;137(49):15426-9. doi: 10.1021/jacs.5b11540. Epub 2015 Dec 3.

Authors

Yanran Ai¹, Mariya V Kozytska¹, Yike Zou¹, Anton S Khartulyari¹, Amos B Smith 3rd¹

Affiliation

¹ Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.

Abstract

A highly convergent, stereocontrolled total synthesis of the architecturally complex marine sponge metabolite (-)-enigmazole A has been achieved. Highlights include an unprecedented late-stage large-fragment Petasis-Ferrier union/rearrangement, a multicomponent Type I Anion Relay Chemistry (ARC) tactic, and a dithiane-epoxide union in conjunction with an oxazole-directed stereoselective reduction.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Structure
Organophosphorus Compounds / chemical synthesis*
Organophosphorus Compounds / chemistry
Oxazoles / chemical synthesis*
Oxazoles / chemistry

Substances

Macrolides
Organophosphorus Compounds
Oxazoles
enigmazole A

Abstract

Publication types

MeSH terms

Substances

Grants and funding