Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
Org Lett. 2022 Jun 24;24(24):4305-4309. doi: 10.1021/acs.orglett.2c00689. Epub 2022 May 10.
A synthesis of 3--hypatulin B, a highly oxygenated and densely functionalized bicyclic scaffold, is reported. The carbon skeleton was prepared by functionalization of a cyclopentanone and an intramolecular Mukaiyama aldol reaction. Highlights include a late-stage photo-oxidation of a methoxyallene to provide an ester group. The problems encountered in the batch process were solved by translation into a flow protocol. Our synthesis highlights the value of flow chemistry to enable challenging late-stage transformations in natural product synthesis.
本文报道了高度氧化和高度官能化的双环骨架 3--hypatulin B 的全合成。该碳骨架通过环戊酮的官能化和分子内 Mukaiyama 羟醛反应制备。其中的亮点包括通过对甲氧基烯丙基的后期光氧化来提供酯基。通过转化为流动方案解决了分批过程中遇到的问题。我们的合成突出了流动化学在天然产物合成中实现挑战性后期转化的价值。
