Department of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, USA.
J Org Chem. 2010 Jan 1;75(1):226-8. doi: 10.1021/jo9020375.
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.
(+/-)-grandisol 的八步合成法的关键步骤涉及到高产率的微波辅助烯炔复分解反应,生成 1-烯基环丁烯,然后将其部分氢化生成硅保护基的 grandisol。复分解催化剂筛选揭示了一个有趣的趋势,即底物转化率与催化剂上配体的特性密切相关。此外,还描述了 1-烯基环丁烯对氢化反应的新反应性。