Synthesis of an analog of mycothiazole and total synthesis of pseudotrienic acid B

被引:10
作者
Amans, Dominique [1 ]
Le Flohic, Alexandre [1 ]
Bellosta, Veronique [1 ]
Meyer, Christophe [1 ]
Cossy, Janine [1 ]
机构
[1] Ecole Super Phys & Chim Ind Ville Paris, CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
natural products; total synthesis; ring-closing metathesis; cross-metathesis; crotyltitanation;
D O I
10.1351/pac200779040677
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An analog of mycothiazole and pseudotrienic acid B were synthesized efficiently by using ring-closing metathesis or cross-metathesis as key reactions.
引用
收藏
页码:677 / 684
页数:8
相关论文
共 18 条
[1]   Total synthesis of pseudotrienic acid B:: A bioactive metabolite from Pseudomonas sp MF 381-IODS [J].
Amans, Dominique ;
Bellosta, Veronique ;
Cossy, Janine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5870-5874
[2]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938
[3]   MYCOTHIAZOLE, A POLYKETIDE HETEROCYCLE FROM A MARINE SPONGE [J].
CREWS, P ;
KAKOU, Y ;
QUINOA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4365-4368
[4]  
Cutignano A, 2001, EUR J ORG CHEM, V2001, P775
[5]   ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES [J].
HAFNER, A ;
DUTHALER, RO ;
MARTI, R ;
RIHS, G ;
ROTHESTREIT, P ;
SCHWARZENBACH, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2321-2336
[6]  
Karsch S, 2002, SYNLETT, P2019
[7]   A recyclable Ru-based metathesis catalyst [J].
Kingsbury, JS ;
Harrity, JPA ;
Bonitatebus, PJ ;
Hoveyda, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :791-799
[8]   Total synthesis of (+-)-mycothiazole and formal enantioselective approach [J].
Le Flohic, A ;
Meyer, C ;
Cossy, J .
ORGANIC LETTERS, 2005, 7 (02) :339-342
[9]  
Le Flohic A, 2003, SYNLETT, P667
[10]   Reactivity of unsaturated sultones synthesized from unsaturated alcohols by ring-closing metathesis. Application to the racemic synthesis of the originally proposed structure of mycothiazole [J].
Le Flohic, Alexandre ;
Meyer, Christophe ;
Cossy, Janine .
TETRAHEDRON, 2006, 62 (38) :9017-9037