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

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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.
Publisher
AMER CHEMICAL SOC
Issue Date
2017-05
Language
English
Article Type
Article
Keywords

DIMERIC INDOLIZIDINE ALKALOIDS; MORITA-BAYLIS-HILLMAN; FLUEGGEA-VIROSA; SECURINEGA ALKALOIDS; CYCLOISOMERIZATION; INCARVIDITONE; DISCOVERY

Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.139, no.18, pp.6302 - 6305

ISSN
0002-7863
DOI
10.1021/jacs.7b02751
URI
http://hdl.handle.net/10203/223953
Appears in Collection
CH-Journal Papers(저널논문)
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