Analogies between synthetic and biosynthetic reactions in which [1,2]-alkyl shifts are combined with other events: dyotropic, Schmidt, and carbocation rearrangements

Osvaldo Gutierrez; Dean J Tantillo

doi:10.1021/jo301864h

Analogies between synthetic and biosynthetic reactions in which [1,2]-alkyl shifts are combined with other events: dyotropic, Schmidt, and carbocation rearrangements

J Org Chem. 2012 Oct 19;77(20):8845-50. doi: 10.1021/jo301864h. Epub 2012 Sep 28.

Authors

Osvaldo Gutierrez¹, Dean J Tantillo

Affiliation

¹ Department of Chemistry, Univeristy of California-Davis, 1 Shields Avenue, Davis, California 95616, USA.

PMID: 23006240
DOI: 10.1021/jo301864h

Abstract

A survey of computational studies on the mechanisms of dyotropic, Schmidt, and related reactions is presented. Connections between synthetically applied versions of these processes and those predicted to occur during biosynthetic terpene-forming carbocation cascades are highlighted.

Publication types

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

MeSH terms

Molecular Conformation
Terpenes / chemical synthesis*
Terpenes / chemistry
Terpenes / metabolism*

Substances

Terpenes