Synlett 2017; 28(12): 1449-1452
DOI: 10.1055/s-0036-1588788
letter
© Georg Thieme Verlag Stuttgart · New York

Efficient Total Synthesis of (±)-Isoguaiacin and (±)-Isogalbulin

Lisa I. Pilkington, Soo Min Song, Bruno Fedrizzi, David Barker*
  • School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand   Email: d.barker@auckland.ac.nz
Further Information

Publication History

Received: 06 March 2017

Accepted after revision: 21 March 2017

Publication Date:
19 April 2017 (eFirst)

Abstract

1-Arylnaphthalene lignans such as (–)-isoguaiacin and (–)-isogalbulin have been reported to exhibit notable biological properties. While (–)-isoguaiacin has not been previously synthesized, syntheses of (–)-isogalbulin are generally long and produce a mixture of stereoisomers. We herein present the efficient total synthesis of (±)-isoguaiacin and (±)-isogalbulin in seven and eight steps with an overall yield of 46% and 36%, respectively. The reported approach harnesses a hydrogenolysis reaction in acidic conditions, to convert a furan into an arylnaphthalen structure.