New Synthetic Routes to (+)-Uleine and (−)-Tubifolidine: General Approach to 2‑Azabicyclo[3.3.1]nonane Indole Alkaloids

Novel asymmetric synthetic routes to (+)-uleine and (−)-tubifolidine are reported herein. The regioselective formation of enol triflates from 2-azabicyclo[3.3.1]­nonane ketones followed by indolizations of the resultant ene-hydrazides allowed the efficient construction of key indole intermediates, f...

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Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (9), p.3464-3468
Main Authors: Kim, Dong-Hyun, Kim, Jeong-Hwa, Jeon, Tae-Hong, Cho, Cheon-Gyu
Format: Article
Language:English
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Summary:Novel asymmetric synthetic routes to (+)-uleine and (−)-tubifolidine are reported herein. The regioselective formation of enol triflates from 2-azabicyclo[3.3.1]­nonane ketones followed by indolizations of the resultant ene-hydrazides allowed the efficient construction of key indole intermediates, facilitating the total synthesis of the target natural alkaloids.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00912