Strategies for the Total Asymmetric Synthesis of Heliannuols K and L: Scope and Limitations
作者:Frédéric Lecornué、Renée Paugam、Jean Ollivier
DOI:10.1002/ejoc.200400908
日期:2005.6
syntheses of certain compounds in racemic form seem accessible, however, improvements through new strategies are still required for the total asymmetric synthesis. This article describes the first synthesis of enantiomerically enriched OMe-heliannuol K and the first stereo- and enantioselective synthesis of heliannuol L, and new approaches and studies of their limitations in the preparation of these
带有末端双键的氧杂酯的 Kulinkovich 反应通过分子内环化得到环丙醇。这些可以进行 Saegusa 氧化以提供 β-氯-氧杂环烷酮,然后可以脱卤化氢为氧杂环烯酮。通过明智地选择起始酯,可以获得具有倍半萜烯基本骨架的各种芳基稠合苯并氧杂环酮,例如向日葵醇。尽管外消旋形式的某些化合物的合成似乎是可行的,但是,对于全不对称合成仍然需要通过新策略进行改进。本文描述了对映体富集的 OMe-heliannuol K 的首次合成和 heliannuol L 的首次立体选择性和对映选择性合成,并详细介绍了它们在制备这些产品中的局限性的新方法和研究。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)