An Efficient Synthesis of (+/-)-Grandisol Featuring 1,5-Enyne Metathesis

作者:Graham Thomas J A; Gray Erin E; Burgess James M; Goess Brian C*
来源:Journal of Organic Chemistry, 2010, 75(1): 226-228.
DOI:10.1021/jo9020375

摘要

An eight-step synthesis of (+/-)-grandisol features a key sequence involving a high-yielding, microwave-assisted enyne metathesis to yield a 1-alkenylcyclobutene that is semihydrogenated to yield a silyl-protected grandisol. Metathesis catalyst screens revealed an intriguing trend whereby substrate conversion correlated strongly with the identity of the ligands on the catalyst. In addition, new reactivity of 1-alkenylcyclobutenes toward hydrogenation is described.

  • 出版日期2010-1-1