Journal
HETEROCYCLES
Volume 103, Issue 2, Pages 687-693Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-20-S(K)65
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Funding
- Toray Science Foundation
- Naito Foundation
- Futaba Electronics Memorial Foundation
- Takeda Science Foundation
- JSPS KAKENHI [JP18H02550, 18K05098]
- Grants-in-Aid for Scientific Research [18K05098] Funding Source: KAKEN
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This study explores the chemical synthesis of the core structure of Didymeline. A tricyclic molecule containing a spiro ring system was successfully synthesized, and enantioselective reactions under silver catalysis were investigated.
Didymeline is an alkaloid with an azaspiro tricyclic skeleton with various functionalities. Despite the fact that its unique architecture is synthetically attractive, its total synthesis has never been achieved before. Herein, we present synthetic studies on the core structure of didymeline. Accordingly, a spiro ring system was constructed through dearomatization of a phenol derivative with alpha-diazoamide unit. Based on the resulting 2-azaspiro[4,5]decane variant, a tricyclic molecule was synthesized via base-promoted intramolecular ring closure. For an asymmetric synthesis, an enantioselective dearomatization was also examined under silver catalysis, which led to the formation of an all-carbon substituted quaternary stereogenic center.
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