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

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초록

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.

키워드

FORMAL TOTAL-SYNTHESISENANTIOSELECTIVE TOTAL SYNTHESESCATALYTIC ASYMMETRIC-SYNTHESISSTRYCHNOS ALKALOIDSFISCHER INDOLIZATIONFUNCTIONALIZED 2-AZABICYCLO<3.3.1>NONANESAKUAMMILINE ALKALOIDSENTRY(-)-STRYCHNINE(+)-ASPIDOSPERMIDINE
제목
New Synthetic Routes to (+)-Uleine and (-)-Tubifolidine: General Approach to 2-Azabicyclo[3.3.1]nonane Indole Alkaloids
저자
Kim, Dong-HyunKim, Jeong-HwaJeon, Tae-HongCho, Cheon-Gyu
DOI
10.1021/acs.orglett.0c00912
발행일
2020-05
유형
Article
저널명
Organic Letters
22
9
페이지
3464 ~ 3468