A new ring expansion for a chiral hexahydroazulene skeleton possessing an angular methyl group

Masaatsu Adachi; Takema Komada; Toshio Nishikawa

doi:10.1021/jo201153h

A new ring expansion for a chiral hexahydroazulene skeleton possessing an angular methyl group

J Org Chem. 2011 Aug 19;76(16):6942-5. doi: 10.1021/jo201153h. Epub 2011 Jul 13.

Authors

Masaatsu Adachi¹, Takema Komada, Toshio Nishikawa

Affiliation

¹ Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan. madachi@agr.nagoya-u.ac.jp

PMID: 21721521
DOI: 10.1021/jo201153h

Abstract

A new synthetic route for a pseudoguaiane ring system is described. The synthesis features an Ireland-Claisen rearrangement for constructing the trans-fused ring system, followed by a new ring expansion to yield a bicyclo[5.3.0]decane ring system possessing an angular methyl group.

Publication types

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

MeSH terms

Azulenes / chemistry*
Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry
Cyclization
Molecular Structure
Stereoisomerism

Substances

Azulenes
Bridged Bicyclo Compounds
bicyclo(5.3.0)decane