Ene-hydrazide from Enol Triflate for the Regioselective Fischer Indole Synthesis

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초록

Ene-hydrazide prepared from enol triflate undergoes a Fischer indolization reaction to give the corresponding indole with complete regioselectivity. The starting enol triflate is readily accessed in regiochemically defined form from the ketone precursor via various well-established methods. This new protocol was successfully applied to the synthesis of desbromoarborescidine A, a natural beta-carboline alkaloid, difficult to prepare with conventional Fischer indole synthesis.

키워드

ENANTIOSELECTIVE SYNTHESISCOUPLING REACTIONSARYL HYDRAZIDESDERIVATIVESSYSTEMREARRANGEMENTCOMBINATIONBROMIDESIODIDESHALIDES
제목
Ene-hydrazide from Enol Triflate for the Regioselective Fischer Indole Synthesis
저자
Lim, Byeong-YunJung, Bo-EunCho, Cheon-Gyu
DOI
10.1021/ol502031q
발행일
2014-09
유형
Article
저널명
Organic Letters
16
17
페이지
4492 ~ 4495