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Stereocontrolled Synthesis of the Tricyclic ABC Ring System of Daphnicyclidin A

ORGANIC LETTERS (2014)

期刊

ORGANIC LETTERS

卷 16, 期 7, 页码 1956-1959

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol5005092

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Chemistry, Organic

资金

National Science Foundation [CHE1055441]
Direct For Mathematical & Physical Scien
Division Of Chemistry [1055441] Funding Source: National Science Foundation

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Reagent

摘要

An enantiocontrolled synthesis pathway has been developed to provide formation of tricyclic amine 7, representing the ABC ring system of the complex alkaloid daphnicyclidin A (1). Our efforts describe preparation of the Z-hexahydro-(1H)-azocine 29 and cyclization to construct the novel 4-azabicyclo[5.3.2]dodecane 31. Transannular reductive amination following the deprotection of 31 gave the desired tertiary amine 7.

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