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A Novel Synthesis of (−)-Huperzine A via Tandem Intramolecular Aza-Prins Cyclization–Cyclobutane Fragmentation

✍ Scribed by White, James D.; Li, Yang; Kim, Jungchul; Terinek, Miroslav


Book ID
120230312
Publisher
American Chemical Society
Year
2013
Tongue
English
Weight
355 KB
Volume
15
Category
Article
ISSN
1523-7060

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The novel pyrrolobenzodiazocine (1) has been prepared by an intramolecular Staudinger/aza Wittig protocol from the precursor azido aldehyde (2) in a remarkable 93% yield. Aldehyde (2) was prepared by coupling protected homoprolinol with 2-azidobenzoic acid followed by deprotection and oxidation.