Synthesis of the C-Terminal Macrocycle of Asperipin-2a

被引：6

作者：

Shabani, Sadegh ^{[1
,2
]}

White, Jonathan M. ^{[1
,2
]}

Hutton, Craig A. ^{[1
,2
]}

机构：

[1] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

[2] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 06期

基金：

澳大利亚研究理事会;

关键词：

ANTIMITOTIC CYCLIC-PEPTIDES; FALSE SMUT BALLS; NATURAL-PRODUCTS; USTILOXIN B; LEWIS-ACID; AZIRIDINE; TRYPTOPHAN; PHENYLALANINE; CYCLIZATION;

D O I：

10.1021/acs.orglett.9b00488

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic approach to the C-terminal macrocycle of asperipin-2a is presented. Two epimers were prepared, possessing R- and S-configurations at the beta-position of Tyr(3). Comparison of NMR data of the natural product with these isomers and X-ray crystallographic data for one macrocycle support assignment of the 2S,3S-configuration of Tyr(3). Key steps in the synthesis include a stereoselective benzylic oxidation of the tyrosine residue and Lewis-acid-catalyzed ring opening of the subsequently generated aziridine.

引用

页码：1877 / 1880

页数：4

共 30 条

[1] Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature [J].

Arnison, Paul G. ;

Bibb, Mervyn J. ;

Bierbaum, Gabriele ;

Bowers, Albert A. ;

Bugni, Tim S. ;

Bulaj, Grzegorz ;

Camarero, Julio A. ;

Campopiano, Dominic J. ;

Challis, Gregory L. ;

Clardy, Jon ;

Cotter, Paul D. ;

Craik, David J. ;

Dawson, Michael ;

Dittmann, Elke ;

Donadio, Stefano ;

Dorrestein, Pieter C. ;

Entian, Karl-Dieter ;

Fischbach, Michael A. ;

Garavelli, John S. ;

Goeransson, Ulf ;

Gruber, Christian W. ;

Haft, Daniel H. ;

Hemscheidt, Thomas K. ;

Hertweck, Christian ;

Hill, Colin ;

Horswill, Alexander R. ;

Jaspars, Marcel ;

Kelly, Wendy L. ;

Klinman, Judith P. ;

Kuipers, Oscar P. ;

Link, A. James ;

Liu, Wen ;

Marahiel, Mohamed A. ;

Mitchell, Douglas A. ;

Moll, Gert N. ;

Moore, Bradley S. ;

Mueller, Rolf ;

Nair, Satish K. ;

Nes, Ingolf F. ;

Norris, Gillian E. ;

Olivera, Baldomero M. ;

Onaka, Hiroyasu ;

Patchett, Mark L. ;

Piel, Joern ;

Reaney, Martin J. T. ;

Rebuffat, Sylvie ;

Ross, R. Paul ;

Sahl, Hans-Georg ;

Schmidt, Eric W. ;

Selsted, Michael E. .

NATURAL PRODUCT REPORTS, 2013, 30 (01) :108-160

[2] Aziridine-Mediated Ligation at Phenylalanine and Tryptophan Sites [J].

Bajaj, Kiran ;

Sakhuja, Rajeev .

CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (15) :1869-1874

[3]

Bennani YL, 1998, SYNLETT, P754

[4] Synthesis of (-)-conocarpan by two routes based on radical cyclization and establishment of its absolute configuration [J].

Clive, Derrick L. J. ;

Stoffman, Elia J. L. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (10) :1831-1842

[5] Ribosomally synthesized and post-translationally modified peptide natural product discovery in the genomic era [J].

Hetrick, Kenton J. ;

van der Donk, Wilfred A. .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2017, 38 :36-44

[6] USTILOXINS, ANTIMITOTIC CYCLIC-PEPTIDES FROM FALSE SMUT BALLS ON RICE PANICLES CAUSED BY USTILAGINOIDEA VIRENS [J].

KOISO, Y ;

LI, Y ;

IWASAKI, S ;

HANAOKA, K ;

KOBAYASHI, T ;

SONODA, R ;

FUJITA, Y ;

YAEGASHI, H ;

SATO, Z .

JOURNAL OF ANTIBIOTICS, 1994, 47 (07) :765-773

[7] Isolation and structure of an antimitotic cyclic peptide, Ustiloxin F: Chemical interrelation with a homologous peptide, Ustiloxin B [J].

Koiso, Y ;

Morisaki, N ;

Yamashita, Y ;

Mitsui, Y ;

Shirai, R ;

Hashimoto, Y ;

Iwasaki, S .

JOURNAL OF ANTIBIOTICS, 1998, 51 (04) :418-422

[8] USTILOXIN - A PHYTOTOXIN AND A MYCOTOXIN FROM FALSE SMUT BALLS ON RICE PANICLES [J].

KOISO, Y ;

NATORI, M ;

IWASAKI, S ;

SATO, S ;

SONODA, R ;

FUJITA, Y ;

YAEGASHI, H ;

SATO, Z .

TETRAHEDRON LETTERS, 1992, 33 (29) :4157-4160

[9] Evolution of the total syntheses of ustiloxin natural products and their analogues [J].

Li, Pixu ;

Evans, Cory D. ;

Wu, Yongzhong ;

Cao, Bin ;

Hamel, Ernest ;

Joullie, Madeleine M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (07) :2351-2364

[10] Trisubstituted aziridine ring-opening by phenol derivatives:: Stereo- and regioselective formation of chiral tertiary alkyl-aryl ethers [J].

Li, Pixu ;

Forbeck, Erin M. ;

Evans, Cory D. ;

Joullie, Madeleine M. .

ORGANIC LETTERS, 2006, 8 (22) :5105-5107

← 1 2 3 →