Formal total synthesis of (+)-gephyrotoxin

被引：57

作者：

Santarem, Marco ^{[1
]}

Vanucci-Bacque, Corinne ^{[1
]}

Lhommet, Gerard ^{[1
]}

机构：

[1] Univ Paris 06, UPMC, CNRS, Equipe Chim Heterocycles,Lab Chim Organ,UMR 7611, F-75005 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期

关键词：

D O I：

10.1021/jo801150e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient formal total synthesis of (+)-gephyrotoxin is described. The key step of our strategy relies on the diastereoselective reduction of a chiral pyrrolidine beta-enamino ester obtained by condensation of (S)-phenylglycinol on a protected 8-hydroxy-3,6-dioxooctanoate.

引用

页码：6466 / 6469

页数：4

共 50 条

[1] TOTAL SYNTHESIS OF (+/-)-GEPHYROTOXIN
FUJIMOTO, R
KISHI, Y
BLOUNT, JF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (23) : 7154 - 7156
[2] A formal total synthesis of (+/-)-gephyrotoxin via the intramolecular Schmidt reaction.
Fang, WK
Pearson, WH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 556 - ORGN
[3] FORMAL SYNTHESIS OF GEPHYROTOXIN 287C
Takashima, Katsuki
Toyooka, Naoki
HETEROCYCLES, 2019, 99 (01) : 649 - 660
[4] Chemoenzymatic enantioselective formal synthesis of (-)-gephyrotoxin-223
Mohammadi Ziarani, Ghodsi
Chenevert, R.
Badiei, Ali Reza
IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2006, 25 (01): : 31 - 38
[5] STUDY TOWARD THE TOTAL SYNTHESIS OF GEPHYROTOXIN
PEARSON, WH
POON, YF
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 112 - ORGN
[6] An enantioselective formal synthesis of (+)-Gephyrotoxin 287C
Miao, Lei
Shu, Hong
Noble, April R.
Fournet, Steven P.
Stevens, Edwin D.
Trudell, Mark L.
ARKIVOC, 2010, : 6 - 14
[7] A Cascade Strategy Enables a Total Synthesis of (-)-Gephyrotoxin
Chu, Shuyu
Wallace, Stephen
Smith, Martin D.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (50) : 13826 - 13829
[8] Establishing methodology to be used in the total synthesis of Gephyrotoxin
Dinsmore, Jason M.
Comins, Daniel L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3022 - U3022
[9] Total synthesis of (-)-gephyrotoxin via a cascade approach
Chu, Shuyu
Wallace, Stephen
Smith, Martin
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
[10] ORGN 122-Total synthesis of (+)-gephyrotoxin
Shu, Hong
Trudell, Mark L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235

← 1 2 3 4 5 →