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- Title
Synthetic Modulation of an Unstable Dehydrosecodine‐type Intermediate and Its Encapsulation into a Confined Cavity Enable Its X‐ray Crystallographic Observation.
- Authors
Tay, Gavin; Wayama, Toshiaki; Takezawa, Hiroki; Yoshida, Satoshi; Sato, Sota; Fujita, Makoto; Oguri, Hiroki
- Abstract
Numerous indole alkaloids such as the iboga‐ and aspidosperma‐type are believed to be biosynthesized via a common hypothetical intermediate, dehydrosecodine. The highly reactive nature of dehydrosecodine‐type compounds has hampered their isolation and structural elucidation. In this study, we achieved the first X‐ray structural determination of a dehydrosecodine‐type compound by integrating synthetic optimization of the reactivity and stabilizing the fragile molecule by encapsulation into a supramolecular host. Formation of a 1 : 1 complex of the dehydrosecodine‐type labile guest bearing both vinyl indole and dihydropyridine units with the host was observed. This integrated approach not only provides insights into the biosynthetic conversions but also allows stabilization and storage of the reactive and otherwise short‐lived intermediate within the confined hydrophobic cavity.
- Subjects
INDOLE alkaloids; X-rays; DIHYDROPYRIDINE; INDOLE
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 32, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202305122