Synthesis of the core structure of acutumine

Matthew D Reeder; G S C Srikanth; Spencer B Jones; Steven L Castle

doi:10.1021/ol050020b

Synthesis of the core structure of acutumine

Org Lett. 2005 Mar 17;7(6):1089-92. doi: 10.1021/ol050020b.

Authors

Matthew D Reeder¹, G S C Srikanth, Spencer B Jones, Steven L Castle

Affiliation

¹ Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.

PMID: 15760146
DOI: 10.1021/ol050020b

Abstract

[reaction: see text] The tricyclic core of the bioactive natural product acutumine has been synthesized. Key steps include an oxidative phenolic coupling to form a masked o-benzoquinone, an anionic oxy-Cope rearrangement to construct an all-carbon quaternary center, and a Michael-type cyclization to form an amine-bearing quaternary carbon. The target compound exists in solution as an enol, in contrast to related compounds that are ketones. A model explaining these observations is presented.

Publication types

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

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry*
Cyclization
Models, Molecular*
Molecular Structure
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry*

Substances

Alkaloids
Spiro Compounds
acutumine