Stereodivergent Total Synthesis of Hapalindoles, Fischerindoles, Hapalonamide H, and Ambiguine H Alkaloids by Developing a Biomimetic, Redox-Neutral, Cascade Prins-Type Cyclization

A stereoselective, redox-neutral, Brønsted acid-catalyzed cascade Prins-type cyclization between indole and aldehyde is described to access several structurally diverse indole terpenoid scaffolds in a single step. Applying this concept, stereodivergent total syntheses of nine hapalindole-type alkalo...

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Bibliographic Details
Published in:Organic letters 2018-10, Vol.20 (20), p.6485-6489
Main Authors: Sahu, Samrat, Das, Beauty, Maji, Modhu Sudan
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Benzenesulfonates - chemistry
Biomimetics
Boronic Acids - chemistry
Cyclization
Indole Alkaloids - chemical synthesis
Indoles - chemical synthesis
Indoles - chemistry
Oxidation-Reduction
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Summary:A stereoselective, redox-neutral, Brønsted acid-catalyzed cascade Prins-type cyclization between indole and aldehyde is described to access several structurally diverse indole terpenoid scaffolds in a single step. Applying this concept, stereodivergent total syntheses of nine hapalindole-type alkaloids are accomplished. Key transformations include allylation using geometrically isomeric allylboronic acid followed by a p-toluenesulfonic acid mediated deprotection–cyclization cascade.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02804