Convergent Strategy to Dizocilpine MK-801 and Derivatives

K. Harsha Vardhan Reddy; Expédite Yen-Pon; Sylvia Cohen-Kaminsky; Samir Messaoudi; Mouad Alami

doi:10.1021/acs.joc.8b00305

Convergent Strategy to Dizocilpine MK-801 and Derivatives

K. Harsha Vardhan Reddy
, Expédite Yen-Pon
, Sylvia Cohen-Kaminsky
, Samir Messaoudi
, Mouad Alami

Université Paris-Sud
Centre Chirurgical Marie-Lannelongue
Faculté de Médecine
Université Paris-Saclay

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	4264-4269
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	83
Issue number	7
DOIs	https://doi.org/10.1021/acs.joc.8b00305
Publication status	Published - 6 Apr 2018
Externally published	Yes

Access to Document

10.1021/acs.joc.8b00305

Cite this

@article{7370202ec63f48dab9bad6b4a62d2ba5,

title = "Convergent Strategy to Dizocilpine MK-801 and Derivatives",

abstract = "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.",

author = "\{Vardhan Reddy\}, \{K. Harsha\} and Exp{\'e}dite Yen-Pon and Sylvia Cohen-Kaminsky and Samir Messaoudi and Mouad Alami",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = apr,

day = "6",

doi = "10.1021/acs.joc.8b00305",

language = "English",

volume = "83",

pages = "4264--4269",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - Convergent Strategy to Dizocilpine MK-801 and Derivatives

AU - Vardhan Reddy, K. Harsha

AU - Yen-Pon, Expédite

AU - Cohen-Kaminsky, Sylvia

AU - Messaoudi, Samir

AU - Alami, Mouad

PY - 2018/4/6

Y1 - 2018/4/6

N2 - 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.

AB - 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.

U2 - 10.1021/acs.joc.8b00305

DO - 10.1021/acs.joc.8b00305

M3 - Article

C2 - 29489358

AN - SCOPUS:85045123564

SN - 0022-3263

VL - 83

SP - 4264

EP - 4269

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

Convergent Strategy to Dizocilpine MK-801 and Derivatives

Abstract

Access to Document

Fingerprint

Cite this