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Rocaglamide是第一个从楝科米仔兰属植物分离得到的环戊烷并苯并呋喃类化合物,有很好的杀虫活性,也是一种极具潜力的抗癌治疗药物。rocaglamide复杂的化学结构和显著的生理活性使其成为极具吸引力的合成靶标。然而,由于环戊烷上有5个相邻的手性中心使得立体选择性合成rocaglamide仍然是具有挑战性的难题。过去几十年,仅有少数完成有关rocaglamide全合成的报道,显示出合成具有rocaglate结构天然产物的难度。本文从分子内环合反应和仿生环加成反应方面综述了rocaglamide的合成方法。
Rocaglamide is the first cyclopentanobenzofuran compound isolated from MeliaSEedia and has good insecticidal activity and is also a potential anticancer drug. The complex chemical structure and significant physiological activity of rocaglamide make it an attractive synthetic target. However, the stereoselective synthesis of rocaglamide remains a challenging problem due to the five adjacent chiral centers on cyclopentane. Over the past few decades, only a few completed reports on total synthesis of rocaglamide have shown the difficulty of synthesizing natural products with the rocaglate structure. This article reviews the synthesis of rocaglamide from intramolecular cyclization and biomimetic cycloaddition reactions.