Total Synthesis and Structure Revision of Boholamide A

被引：6

作者：

Han, Fangzhi ^{[1
]}

Liu, Guangju ^{[1
]}

Zhang, Xuhai ^{[1
]}

Ding, Yahui ^{[1
,2
]}

Wang, Liang ^{[1
,2
]}

Wu, Yijing ^{[3
]}

Chen, Yue ^{[1
,2
]}

Zhang, Quan ^{[1
]}

机构：

[1] Nankai Univ, Coll Pharm, State Key Lab Med Chem Biol, Tianjin 300350, Peoples R China

[2] Nankai Univ, Coll Chem, Tianjin 300071, Peoples R China

[3] Accendatech Co Ltd, Tianjin 300384, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 13期

基金：

中国国家自然科学基金;

关键词：

ABSOLUTE-CONFIGURATION; ASYMMETRIC-SYNTHESIS; CYCLIC DEPSIPEPTIDE; NATURAL-PRODUCTS; RAKICIDIN; MICROTERMOLIDES; VINYLAMYCIN;

D O I：

10.1021/acs.orglett.1c01382

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 15-membered cyclic depsipeptide boholamide A and an epimer were prepared by total synthesis for the first time, thus leading to a revision of C6 stereochemistry in the originally proposed structure of natural boholamide A. This convergent route features achievement of a macro-lactamization step in a gram scale. The revised boholamide A was sythesized with 16 linear steps in 5.46% overall yield. This work facilitates the investigations of boholamide A as a potential hypoxia-selective anticancer agent.

引用

页码：4976 / 4980

页数：5

共 50 条

[1] Total synthesis and structure revision of petrobactin
Bergeron, RJ
Huang, GF
Smith, RE
Bharti, N
McManis, JS
Butler, A
TETRAHEDRON, 2003, 59 (11) : 2007 - 2014
[2] TOTAL SYNTHESIS OF (+/-)-PALUSTRINE AND STRUCTURE REVISION
NATSUME, M
OGAWA, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1984, 32 (09) : 3789 - 3791
[3] Total Synthesis of (-)-Mucosin and Revision of Structure
Nolsoe, Jens M. J.
Antonsen, Simen
Gorbitz, Carl H.
Hansen, Trond V.
Nesman, Jannicke I.
Rohr, Asmund K.
Stenstrom, Yngve H.
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24): : 15066 - 15076
[4] Revision of the Structure and Total Synthesis of Altenuisol
Nemecek, Gregor
Cudaj, Judith
Podlech, Joachim
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (20) : 3863 - 3870
[5] Total Synthesis and Structure Revision of Halioxepine
Poock, Caroline
Kalesse, Markus
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (05) : 1615 - 1619
[6] The total synthesis of (±)-fortucine and a revision of the structure of kirkine
Biechy, Aurelien
Hachisu, Shuji
Quiclet-Sire, Beatrice
Ricard, Louis
Zard, Samir Z.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) : 1436 - 1438
[7] Versicolactones A and B: total synthesis and structure revision
Wang, Liping
Zhu, Weiming
TETRAHEDRON LETTERS, 2013, 54 (49) : 6729 - 6731
[8] Total synthesis and structure revision of Stachybotrys spirolactams
Department of Chemistry, University of Rochester, Rochester, NY 14627, United States
1600, 7422-7427 (September 19, 2003):
[9] Total Synthesis and Structure Revision of Saniculamoid D
Ota, Koichiro
Kamaike, Kazuo
Miyaoka, Hiroaki
SYNLETT, 2023, 34 (19) : 2304 - 2308
[10] Total synthesis and structure revision of chrysamide B
Chen, Jinhong
Li, Junfang
Zhu, Longqing
Peng, Xue
Feng, Yiyue
Lu, Yingmei
Hu, Xiaoling
Liang, Jianpin
Zhao, Quanyi
Wang, Zhen
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (23): : 3402 - 3405

← 1 2 3 4 5 →