Asymmetric Total Syntheses of the Akuammiline Alkaloids (-)-Strictamine and (-)-Rhazinoline

Asymmetric Total Syntheses of the Akuammiline Alkaloids (−)‐Strictamine and (−)‐Rhazinoline

Wenfei Li+, Zhitao Chen+, Di Yu, Xin Peng, GuohuaWen, Siqi Wang, Fei Xue, Xiao-Yu Liu, and Yong Qin*

Angew. Chem. Int. Ed. 2018, 57 (22), 6667–6671

Strictamine and rhazinoline are representative methanoquinolizidine-containing akuammiline alkaloids that possess different stereochemistry at the C16 position. A unified approach to the enantioselective total syntheses of these two molecules is described. The key steps in this synthesis include a photocatalytic intra/intermolecular type II radical cascade reaction, a Tsuji–Trost allylation, a palladium- or nickelmediated cyclization, and a late-stage intramolecular N-alkylation reaction.

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