First Total Synthesis and Stereochemical Revision of Laxaphycin B and Its Extension to Lyngbyacyclamide A

被引：28

作者：

Boyaud, France ^{[1
]}

Mahiout, Zahia ^{[1
]}

Lenoir, Christine ^{[2
]}

Tang, Shoubin ^{[3
]}

Wdzieczak-Bakala, Joanna ^{[2
]}

Witczak, Anne ^{[1
]}

Bonnard, Isabelle ^{[1
]}

Banaigs, Bernard ^{[1
]}

Ye, Tao ^{[4
]}

Inguimbert, Nicolas ^{[1
]}

机构：

[1] Univ Perpignan, Lab Biomol & Environm LCBE, Ctr Phytopharm, F-66860 Perpignan, France

[2] CNRS, Inst Chim Subst Nat, UPR 2301, F-91198 Gif Sur Yvette, France

[3] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Shenzhen 518055, Peoples R China

[4] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 15期

关键词：

ANTIFUNGAL CYCLIC-PEPTIDES; SOLID-PHASE SYNTHESIS; ALGA ANABAENA-LAXA; BIOLOGICAL-PROPERTIES; MARINE CYANOBACTERIA; NATURAL-PRODUCTS; LIPOPEPTIDES;

D O I：

10.1021/ol401645m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of laxaphycin B was accomplished through stepwise automated Solid Phase Peptide Synthesis (SPPS), leading to the structural revision of its stereochemistry especially with regard to the configuration of one of the two 3-hydroxyleucines of this cyclic dodecapeptide of marine origin. The analogous Lyngbyacyclamide A was obtained by an extension of this synthesis.

引用

页码：3898 / 3901

页数：4

共 16 条

[1]

Bonnard I, 1997, LETT PEPT SCI, V4, P289, DOI 10.1007/BF02442891

[2] Total structure and inhibition of tumor cell proliferation of laxaphycins [J].

Bonnard, Isabelle ;

Rolland, Marc ;

Salmon, Jean-Marie ;

Debiton, Eric ;

Barthomeuf, Chantal ;

Banaigs, Bernard .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (06) :1266-1279

[3] Marine cyanobacteria - a prolific source of natural products [J].

Burja, AM ;

Banaigs, B ;

Abou-Mansour, E ;

Burgess, JG ;

Wright, PC .

TETRAHEDRON, 2001, 57 (46) :9347-9377

[4] Towards a biomimetic synthesis of barrenazine A [J].

Buron, Frederic ;

Turck, Alain ;

Plé, Nelly ;

Bischoff, Laurent ;

Marsais, Francis .

TETRAHEDRON LETTERS, 2007, 48 (25) :4327-4330

[5] Impact of Natural Products on Developing New Anti-Cancer Agents [J].

Cragg, Gordon M. ;

Grothaus, Paul G. ;

Newman, David J. .

CHEMICAL REVIEWS, 2009, 109 (07) :3012-3043

[6]

France B., 2013, Tetrahedron Lett, V54, P158, DOI DOI 10.1016/J.TETLET.2012.10.120

[7] ANTIFUNGAL CYCLIC-PEPTIDES FROM THE TERRESTRIAL BLUE-GREEN-ALGA ANABAENA-LAXA .2. STRUCTURES OF LAXAPHYCIN-A LAXAPHYCIN-B, LAXAPHYCIN-D AND LAXAPHYCIN-E [J].

FRANKMOLLE, WP ;

KNUBEL, G ;

MOORE, RE ;

PATTERSON, GML .

JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1458-1466

[8] ANTIFUNGAL CYCLIC-PEPTIDES FROM THE TERRESTRIAL BLUE-GREEN-ALGA ANABAENA-LAXA .1. ISOLATION AND BIOLOGICAL PROPERTIES [J].

FRANKMOLLE, WP ;

LARSEN, LK ;

CAPLAN, FR ;

PATTERSON, GML ;

KNUBEL, G ;

LEVINE, IA ;

MOORE, RE .

JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1451-1457

[9] Total Synthesis and Stereochemical Reassignment of Bisebromoamide [J].

Gao, Xuguang ;

Liu, Yuqing ;

Kwong, Shuqin ;

Xu, Zhengshuang ;

Ye, Tao .

ORGANIC LETTERS, 2010, 12 (13) :3018-3021

[10]

Hale K., 1994, TETRAHEDRON, V50, P9181

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