2-Arylcyclopropylmethanol as a substitute for homoallyl aryl alcohol in the construction of cis-2,6-disubstituted tetrahydropyran: synthesis of (±)-centrolobine

Chem Commun (Camb). 2014 Dec 18;50(97):15457-60. doi: 10.1039/c4cc07796b. Epub 2014 Oct 30.

Abstract

The application of 2-arylcyclopropylmethanols as substitutes to homoallyl aryl alcohols and their reactions with aliphatic aldehydes in the presence of SnCl4 in CH2Cl2 leads to an efficient Prins cyclization to generate cis-2,6-disubstituted tetrahydropyrans in high yields. The reaction is free from 2-oxonia-Cope rearrangement. This protocol was used to synthesize (±)-centrolobine in an overall 84% yield over three steps. The protocol holds promise for scaffold generation for medicinal chemistry exploitation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Cyclopropanes / chemistry*
  • Pyrans / chemical synthesis*

Substances

  • Alcohols
  • Cyclopropanes
  • Pyrans
  • centrolobin