A transannular approach toward lycopodine synthesis

Michaela C Vertorano; Kyla L Johnson; Ping He; Zheng Wei; Zhang Wang

doi:10.1038/s41429-019-0155-2

A transannular approach toward lycopodine synthesis

J Antibiot (Tokyo). 2019 Jun;72(6):494-497. doi: 10.1038/s41429-019-0155-2. Epub 2019 Feb 21.

Authors

Michaela C Vertorano¹, Kyla L Johnson¹, Ping He¹, Zheng Wei¹, Zhang Wang²

Affiliations

¹ Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, NY, 12222, USA.
² Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, NY, 12222, USA. zwang9@albany.edu.

PMID: 30792516
DOI: 10.1038/s41429-019-0155-2

Abstract

A transannular reaction was proposed to access the Lycopodium alkaloid lycopodine. A key bicyclic precursor was synthesized via a ring-closing metathesis reaction. Initial evaluations of the transannular aza-Prins reaction to synthesize lycopodine were reported and discussed.

Publication types

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

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Lycopodium / chemistry
Models, Molecular
Molecular Structure
Quinolizines / chemical synthesis*
Quinolizines / chemistry

Substances

Alkaloids
Quinolizines
lycopodine