Total synthesis and stereochemical revision of xiamenmycin A

被引：11

作者：

Jiao, Xiaozhen ^{[1
,2
]}

Yao, Yangyang ^{[1
,2
]}

Yang, Beibei ^{[1
,2
]}

Liu, Xiaoyu ^{[1
,2
]}

Li, Xiaoyu ^{[1
,2
]}

Yang, Hongguang ^{[1
,2
]}

Li, Li ^{[1
,2
]}

Xu, Jun ^{[3
,4
]}

Xu, Minjuan ^{[5
]}

Xie, Ping ^{[1
,2
]}

机构：

[1] Peking Union Med Coll, Beijing Key Lab Active Subst Discovery & Drugabil, State Key Lab Bioact Subst & Funct Nat Med, Inst Mat Med, Beijing 100050, Peoples R China

[2] Chinese Acad Med Sci, Beijing 100050, Peoples R China

[3] Shanghai Jiao Tong Univ, Inst Oceanol, Shanghai 200240, Peoples R China

[4] Shanghai Jiao Tong Univ, State Key Lab Microbial Metab, Shanghai 200240, Peoples R China

[5] Shanghai Jiao Tong Univ, Shanghai Ctr Syst Biomed, Key Lab Syst Biomed, Shanghai 200240, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 05期

基金：

中国国家自然科学基金;

关键词：

DIASTEREOSELECTIVE SYNTHESIS; N-FORMYLSACCHARIN; CO SOURCE; DERIVATIVES; MECHANISMS; FIBROSIS;

D O I：

10.1039/c5ob02476e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The relative and absolute configurations of xiamenmycin A, a benzopyran compound isolated from Streptomyces xiamenensis 318 with a highly potent anti-fibrotic activity, have been characterized through the total synthesis. The key steps include the construction of the 3-chromanol moiety via Sharpless epoxidation followed by regio- and diastereo-selective cyclization and introduction of the threonine moiety at a later stage via Pd-catalysed aminocarbonylation in a one-pot procedure. The stereochemical assignment of natural xiamenmycin A has been accordingly revised to be 2R, 3S, 3'S, 4'R.

引用

页码：1805 / 1813

页数：9

共 25 条

[1] Z-selective Horner-Wadsworth-Emmons reaction of α-substituted ethyl (diarylphosphono)acetates with aldehydes [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8411-8416

[2]

Argade N., 2012, SYNTHESIS-STUTTGART, P3797

[3] Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].

Berova, Nina ;

Di Bari, Lorenzo ;

Pescitelli, Gennaro .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931

[4] Diastereoselective Synthesis of α-Tocopherol: A New Concept for the Formation of Chromanols [J].

Chapelat, Julien ;

Buss, Axel ;

Chougnet, Antoinette ;

Woggon, Wolf-D. .

ORGANIC LETTERS, 2008, 10 (22) :5123-5126

[5] Novel 2-arylbenzofuran derivatives from Artocarpus petelotii [J].

Chen, Lei ;

Jiang, Wei ;

Hou, Ai-Jun .

HELVETICA CHIMICA ACTA, 2006, 89 (05) :1000-1007

[6] STEPWISE MECHANISMS IN THE ENE REACTION OF ALPHA,BETA-UNSATURATED ESTERS WITH N-PHENYL-1,2,4-TRIAZOLINE-3,5-DIONE AND SINGLET OXYGEN - INTERMOLECULAR PRIMARY AND SECONDARY HYDROGEN ISOTOPE EFFECTS [J].

ELEMES, Y ;

FOOTE, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6044-6050

[7] Isolation and absolute configuration of SMTP-0, a simplest congener of the SMTP family nonlysine-analog plasminogen modulators [J].

Hasumi, Keiji ;

Hasegawa, Keiko ;

Kitano, Yoshikazu .

JOURNAL OF ANTIBIOTICS, 2007, 60 (07) :463-468

[8]

Hill J.G., 1985, ORG SYNTH, V63, P66

[9] Myrsinoic acids B, C and F, anti-inflammatory compounds from Myrsine seguinii [J].

Hirota, M ;

Miyazaki, S ;

Minakuchi, T ;

Takagi, T ;

Shibata, H .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2002, 66 (03) :655-659

[10]

Inoue S, 1998, SYNLETT, P679

← 1 2 3 →