Minimal Fluorous Tagging Strategy that Enables the Synthesis of the Complete Stereoisomer Library of SCH725674 Macrolactones

被引：42

作者：

Moretti, Jared D. ^{[1
]}

Wang, Xiao ^{[1
]}

Curran, Dennis P. ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 18期

基金：

美国国家卫生研究院;

关键词：

GERMINATION SELF-INHIBITOR; 4 CANDIDATE STEREOISOMERS; 2,8-DISUBSTITUTED OXOCANE STRUCTURE; DIVERSITY-ORIENTED SYNTHESIS; PHASE MIXTURE SYNTHESIS; ABSOLUTE-CONFIGURATION; FUNGAL AUTOINHIBITOR; STRUCTURE ASSIGNMENT; PSEUDO-GLOEOSPORONE; LACTONE COMPLEX;

D O I：

10.1021/ja302260d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Four mixtures of four fluorous-tagged quasiisomers have been synthesized, demixed, and detagged to make all 16 stereoisomers of the macrocyclic lactone natural product Sch725674. A new bare-minimum tagging pattern needs only two tags one fluorous and one nonfluorous-to encode four isomers. The structure of Sch725674 is assigned as (5R,6S,8R,14R,E)-5,6,8-trihydroxy-14-pentyloxacyclotetradec-3-en-2-one. Various comparisons of spectra of 32 lactones (16 with tags, 16 without) and 16 ester precursors (8 with tags, 8 without) provide insights into when and why related compounds have the same or different spectra.

引用

页码：7963 / 7970

页数：8

共 44 条

[1] TOTAL SYNTHESIS OF (+)-GLOEOSPORONE - ASSIGNMENT OF ABSOLUTE-CONFIGURATION [J].

ADAM, G ;

ZIBUCK, R ;

SEEBACH, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6176-6177

[2] SYNTHESIS OF MEDIUM RING ETHERS .3. DISPROOF OF THE PROPOSED 2,8-DISUBSTITUTED OXOCANE STRUCTURE FOR GLOEOSPORONE - SYNTHESIS OF PSEUDO-GLOEOSPORONE [J].

CARLING, RW ;

CLARK, JS ;

HOLMES, AB ;

SARTOR, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (01) :95-101

[3] STUDIES ON THE SYNTHESIS OF GLOEOSPORONE - SYNTHESIS OF THE PROPOSED 2,8-DISUBSTITUTED OXOCANE STRUCTURE [J].

CARLING, RW ;

HOLMES, AB .

TETRAHEDRON LETTERS, 1986, 27 (50) :6133-6136

[4]

CELMER W D, 1971, Pure and Applied Chemistry, V28, P413, DOI 10.1351/pac197128040413

[5]

Cleator E, 2004, HETEROCYCLES, V62, P619

[6]

Curran D.P., 2004, The Handbook of Fluorous Chemistry, P128

[7] On the proof and disproof of natural product stereostructures: Characterization and analysis of a twenty-eight member stereoisomer library of murisolins and their Mosher ester derivatives [J].

Curran, Dennis P. ;

Zhang, Qisheng ;

Lu, Hejun ;

Gudipati, Venugopal .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9943-9956

[8] A "Shortcut" Mosher Ester Method To Assign Configurations of Stereocenters in Nearly Symmetric Environments. Fluorous Mixture Synthesis and Structure Assignment of Petrocortyne A [J].

Curran, Dennis P. ;

Sui, Bin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (15) :5411-+

[9] Solution-phase mixture synthesis with fluorous tagging en route: Total synthesis of an eight-member stereoisomer library of passifloricins [J].

Curran, DP ;

Moura-Letts, G ;

Pohlman, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (15) :2423-2426

[10] SYNTHESIS OF (-)-GLOEOSPORONE [J].

CURTIS, NR ;

HOLMES, AB ;

LOONEY, MG ;

PEARSON, ND ;

SLIM, GC .

TETRAHEDRON LETTERS, 1991, 32 (04) :537-540

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