Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 9, Pages 5222-5229Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00071
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Marine tricyclic alkaloids lepadiformine and fasicularin, with a unique perhydropyrrolo[2,1-j]quinoline or perhydropyrido[2,1-j]quinoline framework, were synthesized starting from the B ring of the tricyclic system. This approach includes a highly stereocontrolled diallylation of a cyclic enaminoester and subsequent ring-closing metathesis to construct the A/B ring system, which was transformed into key lactams 32 and 33, and amino alcohol 37. Thus, we achieved formal syntheses of (-)-lepadiformines A, C, and (-)-fasicularin in a divergent manner.
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