Diazatricyclic molecules were synthesized from a 4-hydroxyproline derivative. The hydroxy group was transformed into an amino group, onto which an allyl substituent was introduced. Cross-metathesis enabled further substitution on the allyl moiety. Condensation of the resulting 4-aminoproline derivatives with aldehydes generated azomethine ylides that underwent intramolecular cycloaddition to form the tricyclic framework. Functional groups embedded within the tricyclic framework served as handles for further derivatization.
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Yui Irie
Kosuke Mizuno
Nariyoshi Umekubo
Organic Letters
Nagoya University
Kumamoto University
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Irie et al. (Mon,) studied this question.
www.synapsesocial.com/papers/69e07bc12f7e8953b7cbd6e6 — DOI: https://doi.org/10.1021/acs.orglett.6c01039