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

[41] The first enantioselective total synthesis of cyclomyltaylane-5α-ol and determination of its absolute stereochemistry
Hagiwara, H
Sakai, H
Uchiyama, T
Ito, Y
Morita, N
Hoshi, T
Suzuki, T
Ando, M
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (05): : 583 - 591
[42] Enantioselective synthesis and determination of the absolute configuration of natural (-)-elegansidiol
Audran, G
Galano, JM
Monti, H
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (12) : 2293 - 2296
[43] The first total synthesis and revision of absolute stereochemistry of natural cytotoxic lactone cleistanolate
Kesic, Jelena
Kovacevic, Ivana
Popsavin, Mirjana
Benedekovic, Goran
Rodic, Marko V.
Kojic, Vesna
Popsavin, Velimir
BIOORGANIC CHEMISTRY, 2022, 128
[44] Enantioselective Allylic Substitutions in Natural Product Synthesis
Trost, Barry M.
Crawley, Matthew L.
TRANSITION METAL CATALYZED ENANTIOSELECTIVE ALLYLIC SUBSTITUTION IN ORGANIC SYNTHESIS, 2012, 38 : 321 - 340
[45] Enantioselective Synthesis of the Natural Product (S)-Rugulactone
Nagaiah, Burea
Narsaiah, Akkirala Venkat
HELVETICA CHIMICA ACTA, 2013, 96 (10) : 1948 - 1954
[46] ENANTIOSELECTIVE PROTONATION OF ENOLATES IN NATURAL PRODUCT SYNTHESIS
FEHR, C
CHIMIA, 1991, 45 (09) : 253 - 261
[47] Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis
Cravotto, Giancarlo
Giovenzana, Giovanni B.
Palmisano, Giovanni
Penoni, Andrea
Pilati, Tullio
Sisti, Massimo
Stazi, Federica
TETRAHEDRON-ASYMMETRY, 2006, 17 (22) : 3070 - 3074
[48] First total synthesis of (-)-pericosine a from (-)-shikimic acid: Structure revision and determination of the absolute configuration of antitumor natural product pericosine A
Usami, Yoshihide
Horibe, Yusuke
Takaoka, Isao
Ichikawa, Hayato
Arimoto, Masao
SYNLETT, 2006, (10) : 1598 - 1600
[49] Enantioselective total synthesis of epidithiodioxopiperazine natural products
DeLorbe, John E.
Jabri, Salman Y.
Mennen, Steven M.
Zhang, Fang-Li
Overman, Larry E.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[50] Enantioselective total synthesis of natural iridoid lactone
Lee, Sujin
Paek, Seung-Mann
Yun, Hwayoung
Kim, Nam-Jung
Jang, Jaebong
Sim, Jaehoon
Suh, Young-Ger
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243

← 1 2 3 4 5 →