Total Synthesis of (+)-Hyacinthacine A 1 Using a Chemoselective Cross-Benzoin Reaction and a Furan Photooxygenation–Amine Cyclization Strategy

作者：Karnjit Parmar, Pouyan Haghshenas, Michel Gravel · 发表于：Organic Letters · 年份：2021 · DOI：10.1021/acs.orglett.1c00090 · 被引用次数：31 · 研究领域：Carbohydrate Chemistry and Synthesis、Synthetic Organic Chemistry Methods、Synthesis of Indole Derivatives

We report the shortest synthesis of glycosidase inhibitor (+)-hyacinthacine A 1 using a highly chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reaction as well as a furan photooxygenation–amine cyclization strategy. This is the first such cyclization on a furylic alcohol, an unprecedented reaction due to the notorious instability of the formed intermediates. The photooxygenation strategy was eventually incorporated into a three-step one-pot process that formed the requisite pyrrolizidine framework of (+)-hyacinthacine A 1 .