First enantioselective total synthesis of (-)-dysibetaine CPa and absolute configurations of natural product

被引：9

作者：

Sakai, Michihiro ^{[1
]}

Ishikawa, Yuichi ^{[1
]}

Takamizawa, Satoshi ^{[1
]}

Oikawa, Masato ^{[1
]}

机构：

[1] Yokohama City Univ, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 44期

关键词：

Cyclopropane; Dysibetaine CPa; Enantioselective total synthesis; Quaternary ammonium group; Neuroactive natural product; Organocatalytic solvolysis; SPONGE DYSIDEA-HERBACEA; CINCHONA ALKALOIDS; AMINO-ACID; ANHYDRIDES; DYSIHERBAINE;

D O I：

10.1016/j.tetlet.2013.08.113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we report total synthesis of enantiomerically pure dysibetaine CPa, isolated from Micronesian marine sponge and expected to serve as a neuroactive agent. Starting from meso-cyclopropane triester, the synthesis was achieved in 12.8% overall yield over 10 steps including organocatalytic enantioselective solvolysis of meso-succinic anhydride as a key step. This work established the absolute configurations of the natural product as (3R,4R). (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5911 / 5912

页数：2

共 50 条

[31] Total synthesis of (-)-dictyostatin:: Confirmation of relative and absolute configurations
Shin, Y
Fournier, JH
Fukui, Y
Brückner, AM
Curran, DP
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (35) : 4634 - 4637
[32] First enantioselective total synthesis of altersolanol A
Mechsner, Bastian
Henssen, Birgit
Pietruszka, Joerg
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (41) : 7674 - 7681
[33] The first enantioselective total synthesis of (-)-arisugacin A
Cole, KP
Hsung, RP
TETRAHEDRON LETTERS, 2002, 43 (48) : 8791 - 8793
[34] First enantioselective total synthesis of (-)-tejedine
Wang, YC
Georghiou, PE
ORGANIC LETTERS, 2002, 4 (16) : 2675 - 2678
[35] Enantioselective total synthesis and correction of the absolute configuration of megislactone
Ren, Guo-Bao
Wu, Yikang
TETRAHEDRON, 2008, 64 (19) : 4408 - 4415
[36] Enantioselective total synthesis and absolute stereostructure of hippospongic acid A
Hioki, H
Ooi, H
Hamano, M
Mimura, Y
Yoshio, S
Kodama, M
Ohta, S
Yanai, M
Ikegami, S
TETRAHEDRON, 2001, 57 (07) : 1235 - 1246
[37] Enantioselective Total Synthesis and Determination of Absolute Configuration of Vittatalactone
Schmidt, Yvonne
Breit, Bernhard
ORGANIC LETTERS, 2009, 11 (21) : 4767 - 4769
[38] Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Toxicodenane A
Qin, Xu-Long
Wu, Guo-Jie
Han, Fu-She
ORGANIC LETTERS, 2021, 23 (21) : 8570 - 8574
[39] Enantioselective Total Synthesis and Absolute Configuration of Apiosporic Acid
Gaertner, Martin
Kossler, David
Pflaesterer, Daniel
Helmchen, Guenter
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09): : 4491 - 4495
[40] Total Synthesis of Gobiusxanthin Stereoisomers and Their Application to Determination of Absolute Configurations of Natural Products: Revision of Reported Absolute Configuration of Epigobiusxanthin
Yamano, Yumiko
Ematsu, Kotaro
Kurimoto, Hiromasa
Maoka, Takashi
Wada, Akimori
MARINE DRUGS, 2015, 13 (01): : 159 - 172

← 1 2 3 4 5 →