Synthesis of Cardiopetaline via a Wagner-Meerwein Rearrangement without Preactivation of the Pivotal Hydroxy Group

  • Org Lett. 2017 Nov 3;19(21):5833-5835. doi: 10.1021/acs.orglett.7b02812.
Yoshitake Nishiyama  1  2 ,  Satoshi Yokoshima  1 ,  Tohru Fukuyama  1
Affiliations
  • 1. Graduate School of Pharmaceutical Sciences, Nagoya University , Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
  • 2. Graduate School of Pharmaceutical Sciences, University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
PMID: 29039205 DOI: 10.1021/acs.orglett.7b02812
Abstract

A synthesis of cardiopetaline has been accomplished via a Wagner-Meerwein rearrangement of a diol having the denudatine skeleton. The Wagner-Meerwein rearrangement could be facilitated simply by heating the diol with p-toluenesulfonic acid in pivalic acid, without preactivating the pivotal hydroxy group. This strategy does not require differentiation of several hydroxy groups in the substrate for the Wagner-Meerwein rearrangement and could be applied to the synthesis of more highly oxygenated aconitine-type diterpenoid Alkaloids.

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