Total synthesis and biological evaluation of marinopyrrole A and analogs

被引：33

作者：

Nicolaou, K. C. ^{[1
,2
,3
]}

Simmons, Nicholas L. ^{[1
,2
]}

Chen, Jason S. ^{[1
,2
]}

Haste, Nina M. ^{[4
]}

Nizet, Victor ^{[4
,5
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

[4] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92093 USA

[5] Univ Calif San Diego, Dept Pediat, La Jolla, CA 92093 USA

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 17期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

Marine natural products; Total synthesis; Atropisomers; Clauson-Kaas reaction; ANTICANCER AGENTS;

D O I：

10.1016/j.tetlet.2010.09.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A five-step total synthesis of the antibiotic marinopyrrole A (1) is described. The developed synthetic technology enabled the synthesis of several marinopyrrole A analogs whose antibacterial properties against methicillin-resistant Staphylococcus aureus TCH1516 were evaluated. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2041 / 2043

页数：3

共 8 条

[1] Total Synthesis of (±)-Marinopyrrole A and Its Library as Potential Antibiotic and Anticancer Agents
Cheng, Chunwei
Pan, Lili
Chen, Yi
Song, Hao
Qin, Yong
Li, Rongshi
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04): : 541 - 547
[2] Improved syntheses of 3H,5H-pyrrolo[3,2-d]pyrimidines
Furneaux, RH
Tyler, PC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) : 8411 - 8412
[3] HASTE NM, ANTIMICROB AGE UNPUB
[4] The marinopyrroles, antibiotics of an unprecedented structure class from a marine Streptomyces sp.
Hughes, Chambers C.
Prieto-Davo, Alejandra
Jensen, Paul R.
Fenical, William
[J]. ORGANIC LETTERS, 2008, 10 (04) : 629 - 631
[5] Structures, Reactivities, and Antibiotic Properties of the Marinopyrroles A-F
Hughes, Chambers C.
Kauffman, Christopher A.
Jensen, Paul R.
Fenical, William
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (10) : 3240 - 3250
[6] Marinopyrrole A Target Elucidation by Acyl Dye Transfer
Hughes, Chambers C.
Yang, Yu-Liang
Liu, Wei-Ting
Dorrestein, Pieter C.
La Clair, James J.
Fenical, William
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) : 12094 - +
[7] Revised Structure and Synthesis of Celastramycin A, A Potent Innate Immune Suppressor
Kikuchi, Haruhisa
Sekiya, Mizuki
Katou, Yasuhiro
Ueda, Kazunori
Kabeya, Takahiro
Kurata, Shoichiro
Oshima, Yoshiteru
[J]. ORGANIC LETTERS, 2009, 11 (08) : 1693 - 1695
[8] Synthesis and biological evaluation of novel pyrrolopyrrolizinones as anticancer agents
Rochais, C.
Lisowski, V.
Dallemagne, P.
Rault, S.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) : 8162 - 8175

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