Formal Total Synthesis of Manzacidin C Based on Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines | Zendy

Thu Minh Thi Tong | Zendy; Takahiro Soeta | Zendy; Takuya Suga | Zendy; Keisuke Kawamoto | Zendy; Yoshihito Hayashi | Zendy; Yutaka Ukaji | Zendy

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Formal Total Synthesis of Manzacidin C Based on Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines

Author(s) -

Thu Minh Thi Tong,

Takahiro Soeta,

Takuya Suga,

Keisuke Kawamoto,

Yoshihito Hayashi,

Yutaka Ukaji

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.6b02816

Subject(s) - chemistry , enantioselective synthesis , cycloaddition , imine , 1,3 dipolar cycloaddition , total synthesis , stereochemistry , combinatorial chemistry , organic chemistry , catalysis

An enantioselective formal total synthesis of (+)-manzacidin C is described. A key feature of the synthesis is the construction of two chiral centers via the asymmetric 1,3-dipolar cycloaddition of an azomethine imine to methallyl alcohol by the use of (S,S)-DIPT as a chiral auxiliary.

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