Toward the total synthesis of tetrodotoxin: stereoselective construction of the 7-oxanorbornane intermediate

被引：10

作者：

Manabe, Atsushi ^{[1
]}

Ohfune, Yasufumi ^{[1
]}

Shinada, Tetsuro ^{[1
]}

机构：

[1] Osaka City Univ, Grad Sch Sci, Sumiyoshi Ku, Osaka 5588585, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 44期

关键词：

Tetrodotoxin; Diels-Alder reaction; Nitroolefin; Furan; EFFICIENT TOTAL-SYNTHESIS; OPTICALLY-ACTIVE TETRODOTOXIN; ASYMMETRIC TOTAL-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; DIELS-ALDER; CHEMICAL-SYNTHESIS; UNNATURAL ANALOG; D-GLUCOSE; 8,11-DIDEOXYTETRODOTOXIN; DERIVATIVES;

D O I：

10.1016/j.tetlet.2014.09.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of 7-oxanorbornane regarding as a key synthetic intermediate of tetrodotoxin (TTX) is reported. The bicyclo ring bearing various functional groups was successfully elaborated by a furan Diels-Alder (DA) reaction. The stereoselective installation of a quaternary amino carbon center to the DA product was achieved with the Tsuji-Trost allylation. The stereochemistry was unambiguously confirmed with X-ray. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6077 / 6080

页数：4

共 50 条

[21] SYNTHETIC APPROACHES TOWARD NAPHTHYRIDINOMYCIN .1. STEREOSELECTIVE SYNTHESIS OF A TETRACYCLIC INTERMEDIATE
FUKUYAMA, T
LAIRD, AA
TETRAHEDRON LETTERS, 1986, 27 (51) : 6173 - 6176
[22] SYNTHETIC APPROACHES TOWARD MITOMYCINS .1. STEREOSELECTIVE SYNTHESIS OF A TETRACYCLIC INTERMEDIATE
FUKUYAMA, T
YANG, LH
TETRAHEDRON LETTERS, 1986, 27 (52) : 6299 - 6300
[23] A stereoselective route toward polyhydroxylated piperidines.: A total synthesis of (±)-deoxymannojirimycin
Boglio, C
Stahlke, S
Thorimbert, S
Malacria, M
ORGANIC LETTERS, 2005, 7 (22) : 4851 - 4854
[24] Toward a total synthesis of brassinosteroids; stereoselective generation of the hydrindane ring system
Ternmem, O
Zoller, T
Uguen, D
TETRAHEDRON LETTERS, 2002, 43 (17) : 3181 - 3184
[25] Stereoselective construction of the key intermediate for the synthesis of the tetrahydropyranyl antifungal agents (+)-restricticin and (+)-lanomycin
Honda, T.
Satoh, A.
Yamada, T.
Hayakawa, T.
Jornal of the Chemical Society. Perkin Transactions 1, (03):
[26] Stereoselective construction of the key intermediate for the synthesis of the tetrahydropyranyl antifungal agents (+)-restricticin and (+)-lanomycin
Honda, T
Satoh, A
Yamada, T
Hayakawa, T
Kanai, K
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03): : 397 - 405
[27] Toward an enantioselective total synthesis of sarain A: Construction of an advanced intermediate and rearrangement of the sarain A core under mild conditions
Douglas, CJ
Hiebert, S
Overman, LE
ORGANIC LETTERS, 2005, 7 (05) : 933 - 936
[28] Toward the Total Synthesis of Haliclonin A: Construction of a Tricyclic Substructure
Luo, Shi-Peng
Guo, Lian-Dong
Gao, Long-Hui
Li, Shuang
Huang, Pei-Qiang
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (01) : 87 - 91
[29] Progress toward the total synthesis of staurosporine, application of a stereoselective ring expansion to the synthesis of indolocarbazoles
Wood, JL
Stoltz, BM
Onweme, K
Goodman, S
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 205 - ORGN
[30] Study on the total synthesis of hainanolide - Construction of tricyclic intermediate(I)
Zhang, LY
Chen, SZ
Wei, D
Huang, L
Chai, JJ
He, CH
CHINESE CHEMICAL LETTERS, 1996, 7 (10) : 892 - 893

← 1 2 3 4 5 →