Abstract

Development of a route for the synthesis of the core structure of galiellalactone is described. The key step involves a ring-closing enyne metathesis of an allyl propargyl ether to produce a dihydro furano diene with a latent dienophile. The dienophile, when generated from this latent functionality, underwent an in situ intramolecular Diels–Alder reaction to produce the tricyclic skeleton present in galiellalactone.

Graphic Abstract

An approach to the construction of the tricyclic core structure of the fungal metabolite galiellalactone is described using a sequence of ring-closing enyne metathesis and intramolecular Diels–Alder reaction.

中文翻译：

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顺序闭环烯炔复分解和分子内Diels-Alder反应：合成加利拉内酯核心结构的方法

摘要

描述了合成加利拉内酯核心结构的途径的开发。关键步骤涉及烯丙基炔丙基醚的闭环烯炔复分解，以产生具有潜伏的亲二烯体的二氢呋喃基二烯。从这种潜在功能中产生的亲双烯体将进行原位分子内Diels-Alder反应，生成加利拉内酯中存在的三环骨架。

图形摘要

使用一系列闭环烯炔复分解和分子内Diels-Alder反应，描述了构建真菌代谢产物加利拉内酯三环核心结构的方法。