Rocaglamide的合成进展

Advance on synthesis of rocaglamide

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,the first cyclopenta[b]benzofuran derivative from Aglaia elliptifolia,was found to exhibit considerably insecticidal activities and excellent potential as therapeutic candidates in cancer chemotherapy.Both the structural complexity of rocaglamide and its significant activity make it an attractive synthetic target.Stereoselective synthesis of the dense substitution pattern of these targets is a formidable synthetic challenge： the molecules bear five contiguous stereocenters and cis aryl groups on adjacent carbons.In past years of effort,only a handful of completed total syntheses have been reported,evidence of the difficulties associated with the synthesis of rocaglate natural products.This review summarized the progress in the synthesis of rocaglamide from intramolecular cyclizations and biomimetic cycloaddition reaction.