Convergent Strategy to Dizocilpine MK-801 and Derivatives | Zendy

K. Harsha Vardhan Reddy | Zendy; Expédite YenPon | Zendy; Sylvia CohenKaminsky | Zendy; Samir Messaoudi | Zendy; Mouâd Alami | Zendy

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Convergent Strategy to Dizocilpine MK-801 and Derivatives

Author(s) -

K. Harsha Vardhan Reddy,

Expédite YenPon,

Sylvia CohenKaminsky,

Samir Messaoudi,

Mouâd Alami

Publication year - 2018

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.8b00305

Subject(s) - chemistry , alkene , hydroamination , intramolecular force , amine gas treating , heck reaction , intramolecular reaction , amide , convergent synthesis , stereochemistry , imine , combinatorial chemistry , organic chemistry , palladium , catalysis

A convergent total synthesis of MK-801 has been achieved. Key synthetic transformations include a multicomponent Barbier-type reaction to construct the α-branched amine, a selective Heck α-coupling tactic to generate the exocyclic alkene skeleton, and a late-stage intramolecular hydroamination reaction between the exocyclic alkene and the secondary protected amine. The efficacy of this method was demonstrated by the synthesis of two news analogues substituted on the aromatic rings.

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