Total synthesis of a thymidine 2-deoxypolyoxin C analogue

被引：25

作者：

Dehoux, C ^{[1
]}

Fontaine, E ^{[1
]}

Escudier, JM ^{[1
]}

Baltas, M ^{[1
]}

Gorrichon, L ^{[1
]}

机构：

[1] Universite Paul Sabatier, Lab Synthese & Physicochim Organ, CNRS, ESA 5068, F-31062 Toulouse 4, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 08期

关键词：

D O I：

10.1021/jo972116s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the thymidine 2-deoxypolyoxin C analogue 10 from a noncarbohydrate precursor was achieved in 10 steps and 9% yield starting from a chiral gamma,delta-epoxy-beta-hydroxy ester 11 readily available from cis-2-butene-1,4-diol, The main steps concern the stereo-and regioselective opening of the epoxide ring by an azide anion, the stereoselective introduction of the thymine base, and the transformation of the primary alcohol to the acid functionality of the final product. Two other approaches have also been investigated.

引用

页码：2601 / 2608

页数：8

共 50 条

[41] Synthesis of furo[2,3-c]pyran-beta-D-thymidine
Bousquie, I
Madiot, V
Florent, JC
Monneret, C
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (15) : 1815 - 1818
[42] Asymmetric synthesis of machilin C and its analogue
Xia, Yamu
Wang, Wei
CHEMICAL PAPERS, 2010, 64 (05) : 630 - 636
[43] ENZYMATIC SYNTHESIS OF C-14 LABELED THYMIDINE
SEKIGUCHI, T
YOSHIKAWA, H
JOURNAL OF BIOCHEMISTRY, 1959, 46 (11): : 1505 - 1511
[44] Stereoselective synthesis of C-5'-substituted thymidine
Escudier, JM
Tworkowski, I
Bouziani, L
Gorrichon, L
TETRAHEDRON LETTERS, 1996, 37 (27) : 4689 - 4692
[45] Total Synthesis of Pactalactam, an Imidazolidinone-Type Pactamycin Analogue
Kim, Taejung
Matsushita, Shohei
Matsudaira, So
Doi, Tsuyoshi
Hirota, Shinji
Park, Young-Tae
Igarashi, Masayuki
Hatano, Masaki
Ikeda, Noriko
Ham, Jungyeob
Nakata, Masaya
Saikawa, Yoko
ORGANIC LETTERS, 2019, 21 (10) : 3554 - 3557
[46] Enantioselective Total Synthesis of Cannabinoids-A Route for Analogue Development
Shultz, Zachary P.
Lawrence, Grant A.
Jacobson, Jeffrey M.
Cruz, Emmanuel J.
Leahy, James W.
ORGANIC LETTERS, 2018, 20 (02) : 381 - 384
[47] TOTAL SYNTHESIS OF A NUCLEAR ANALOGUE OF PENICILLIN-CEPEHOLOSPORIN ANTIBIOTICS
BRUNWIN, DM
LOWE, G
PARKER, J
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (22): : 3756 - &
[48] Enantioselective Total Synthesis and Biological Evaluation of (+)-Kibdelone A and a Tetrahydroxanthone Analogue
Winter, Dana K.
Endoma-Arias, Mary Ann
Hudlicky, Tomas
Beutler, John A.
Porco, John A., Jr.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15): : 7617 - 7626
[49] Total Synthesis and Structural Revision of Kasumigamide, and Identification of a New Analogue
Kuranaga, Takefumi
Matsuda, Kenichi
Takaoka, Masachika
Tachikawa, Chisato
Sano, Ayae
Itoh, Kosei
Enomoto, Ayumu
Fujita, Kei
Abe, Ikuro
Wakimoto, Toshiyuki
CHEMBIOCHEM, 2020, 21 (23) : 3329 - 3332
[50] Total Synthesis and Cytotoxicity Evaluation of an Oxazole Analogue of Tubulysin U
Sreejith, Shankar P.
Sani, Monica
Saunders, Fiona R.
Wallace, Heather M.
Zanda, Matteo
SYNLETT, 2011, (12) : 1673 - 1676

← 1 2 3 4 5 →