Total Synthesis and Stereochemistry Assignment of Nucleoside Antibiotic A-94964

被引：8

作者：

Shao, Xiaofei ^{[1
,2
]}

Zheng, Chang ^{[1
]}

Xu, Peng ^{[2
]}

Shiraishi, Taro ^{[3
]}

Kuzuyama, Tomohisa ^{[3
,4
]}

Molinaro, Antonio ^{[5
]}

Silipo, Alba ^{[5
]}

Yu, Biao ^{[1
,2
]}

机构：

[1] Univ Chinese Acad Sci, Sch Chem & Mat Sci, Hangzhou Inst Adv Study, Hangzhou, Peoples R China

[2] Chinese Acad Sci, State Key Lab Bioorgan & Nat Prod Chem, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,Univ Chinese Acad Sci, Shanghai, Peoples R China

[3] Univ Tokyo, Grad Sch Agr & Life Sci, Tokyo, Japan

[4] Univ Tokyo, Collaborat Res Inst Innovat Microbiol, Tokyo, Japan

[5] Univ Naples Federico II, Dept Chem Sci, Naples, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 14期

基金：

中国国家自然科学基金;

关键词：

A-94964; Nucleoside Antibiotic; Octuronic Acid Uridine; Phosphodiester; Total Synthesis; BACTERIAL TRANSLOCASE-I; BIOLOGICAL EVALUATION; MODULAR APPROACH; MRAY; GLYCOSYLATION; TUNICAMYCINS; INHIBITOR;

D O I：

10.1002/anie.202200818

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A collective total synthesis of eight diastereoisomers associated with NMR analysis leads to a full stereochemistry assignment of the structurally unique nucleoside antibiotic A-94964, which features an octuronic acid uridine core decorated with an alpha-D-mannopyr-anosyl residue and an alpha-D-N-acylglucosaminopyranosyl residue via a phosphodiester bridge.

引用

页数：7

共 50 条

[21] Optical rotation computation, total synthesis, and stereochemistry assignment of the marine natural product pitiamide A
1600, ACS, Washington, DC, USA (122):
[22] Total Synthesis, Assignment of the Relative and Absolute Stereochemistry, and Structural Reassignment of Phostriecin (aka Sultriecin)
Burke, Christopher P.
Haq, Nadia
Boger, Dale L.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (07) : 2157 - +
[23] Assignment of absolute stereochemistry and total synthesis of (-)-spongidepsin (vol 6, pg 2056, 2004)
Ghosh, AK
Xu, XM
ORGANIC LETTERS, 2004, 6 (14) : 2490 - 2490
[24] Optical rotation computation, total synthesis, and stereochemistry assignment of the marine natural product pitiamide A
Ribe, S
Kondru, RK
Beratan, DN
Wipf, P
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) : 4608 - 4617
[25] The naturally occurring ketene acetal benesudon: Total synthesis and assignment of relative and absolute stereochemistry
Clive, Derrick L. J.
Minaruzzaman
Yang, Haikang
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6743 - 6752
[26] First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry
Hayashi, Y
Shoji, M
Mukaiyama, T
Gotoh, H
Yamaguchi, S
Nakata, M
Kakeya, H
Osada, H
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14): : 5643 - 5654
[27] Total Synthesis, Assignment of the Absolute Stereochemistry, and Structure-Activity Relationship Studies of Subglutinols A and B
Kim, Hyoungsu
Baker, Joseph B.
Park, Yongho
Park, Hyung-Bae
DeArmond, Patrick D.
Kim, Seong Hwan
Fitzgerald, Michael C.
Lee, Dong-Sup
Hong, Jiyong
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (08) : 1902 - 1910
[28] TOTAL SYNTHESIS AND STEREOCHEMISTRY OF HYBRIDALACTONE
COREY, EJ
DE, B
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (09) : 2735 - 2736
[29] DESOXYSCHIZANDRIN, STEREOCHEMISTRY AND TOTAL SYNTHESIS
GHERA, E
BENDAVID, Y
BECKER, D
TETRAHEDRON LETTERS, 1977, (05) : 463 - 466
[30] Total synthesis and stereochemistry of cytoblastin
Moreno, OA
Kishi, Y
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) : 8180 - 8181

← 1 2 3 4 5 →