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Efficient Synthetic Access to the Hetisine C 20 -Diterpenoid Alkaloids. A Concise Synthesis of Nominine via Oxidoisoquinolinium-1,3-Dipolar and Dienamine-Diels−Alder Cycloadditions

2006; American Chemical Society; Volume: 128; Issue: 27 Linguagem: Inglês

10.1021/ja0625430

1943-2984

Kevin M. Peese, David Y. Gin,

Alkaloids: synthesis and pharmacology

A concise synthetic approach to the hetisine C20-diterpenoid alkaloids is reported. The total synthesis of (±)-nominine was accomplished in a 15-step sequence employing a dual cycloaddition strategy. Key features of the synthesis include a reversible intramolecular 4-oxidoisoquinolinium betaine dipolar cycloaddition in conjunction with a pyrrolidine-induced dienamine isomerization/Diels−Alder cascade.