Unified Total Synthesis of Pentacyclic Stemoamide-type Alkaloids

• DOI: 10.1021/acs.orglett.0c02697
• Publication Date: 2020-09-22T14:06:06Z
• Authors: Yasuki Soda; Yasukazu Sugiyama; Makoto Yoritate; Hayato Tajima; Kana Shibuya; Chisato Ogihara; Takeshi Oishi; Takaaki Sato; Noritaka Chida
• Keywords: Pyrrolidine; Pyrrole; Natural product

The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for comprehensive biological profiling these natural products. In this Letter, we report unified seven and two unnatural derivatives. keys to success are (1) the chemoselective assembly four five-membered building blocks, (2) direct oxidation pyrrolidine products pyrrole derivatives, (3) stereodivergent construction totally E- or Z-substituted butenolides.