Asymmetric Synthesis of cis-7-Methoxycalamenene via the Intramolecular Buchner Reaction of an alpha-Diazoketone

作者:McDowell Paul A; Foley David A; O' Leary Patrick; Ford Alan; Maguire Anita R*
来源:Journal of Organic Chemistry, 2012, 77(4): 2035-2040.
DOI:10.1021/jo202499j

摘要

The asymmetric synthesis of cis-7-methoxycalamenene 1 has been accomplished using the intramolecular Buchner reaction of a-diazoketone 7 as the key step in the synthetic route. Upon reduction of the equilibrating azulenone structure 8, the resulting azulenol 9 rearranges to dihydronaphthalene 10 containing the 6,6-membered bicyclic ring system characteristic of 1, by means of an acid-catalyzed aromatization process. Transformation of 10 to 1 is accomplished through a three-step reaction sequence.

  • 出版日期2012-2-17