Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 48, Pages 13215-13219Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201407686
Keywords
alkaloids; aromatic substitution; cross-coupling; cyclization; total synthesis
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Funding
- Cabinet Office, Government of Japan [LS008]
- JSPS KAKENHI [20390003, 26253001]
- Nagase Science and Technology Foundation
- JSPS
- [19790004]
- Grants-in-Aid for Scientific Research [26253001, 12J09526, 20390003] Funding Source: KAKEN
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The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused beta-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the beta-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubia.
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