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분자활성 촉매반응 연구단
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An Accelerated Intermolecular Rauhut-Currier Reaction Enables the Total Synthesis of (-)-Flueggenine C

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Title
An Accelerated Intermolecular Rauhut-Currier Reaction Enables the Total Synthesis of (-)-Flueggenine C
Author(s)
Sangbin Jeon; Sunkyu Han
Publication Date
2017-05
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.139, no.18, pp.6302 - 6305
Publisher
AMER CHEMICAL SOC
Abstract
The first total synthesis of dimeric securinega alkaloid (-)-flueggenine C is completed via an accelerated intermoleculat Rauhut Currier (RC) reaction. Despite the numerous reports on the total synthesis of monomeric securinegas, the synthesis of dimeric securinegas whose monomeric units are connected by a putative enzymatic RC reaction has not been reported to date. We have found that installation of a nucleophilic functional group at the 7-position of an enone greatly accelerates the rate of the diastereoselective intermolecular RC reaction. This discovety enabled an efficient and selective formation of the dimeric intermediate which was further transformed to (-)-flueggenine C © 2017 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/4805
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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