The application of Morita-Baylis-Hillman reaction: Synthetic studies on perophoramidine

A new concise methodology was developed for the synthesis of the two vicinal quaternary centers of the natural product perophoramidine. Key steps involved the Morita–Baylis–Hillman reaction, reductive cyclization and allylic alkylation. Moreover, most conditions are simple and convenient with good y...

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Bibliographic Details
Published inTetrahedron Vol. 73; no. 27-28; pp. 3966 - 3972
Main Authors Wu, Lin, Zhang, Qian-Ru, Huang, Ji-Rong, Li, Yang, Su, Fu, Dong, Lin
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.07.2017
Elsevier
Subjects
Allylic alkylation
Chemistry
Chemistry, Organic
MBH
Physical Sciences
Reductive cyclization
Science & Technology
Vicinal quaternary centers
Allylic alkylation
MBH
Reductive cyclization
Vicinal quaternary centers
CARBONATES
COMMUNESIN F
STRATEGY
QUATERNARY STEREOCENTERS
EFFICIENT SYNTHESIS
DEHALOPEROPHORAMIDINE
ISATIN DERIVATIVES
CONSTRUCTION
(+)-PEROPHORAMIDINE
ALKALOIDS
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Summary:A new concise methodology was developed for the synthesis of the two vicinal quaternary centers of the natural product perophoramidine. Key steps involved the Morita–Baylis–Hillman reaction, reductive cyclization and allylic alkylation. Moreover, most conditions are simple and convenient with good yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.05.067