Total synthesis of FR901483

被引:69
作者
Ousmer, M
Braun, NA
Ciufolini, MA
机构
[1] Univ Lyon 1, LSMO, F-69622 Villeurbanne, France
[2] Ecole Super Chim Phys Elect Lyon, F-69622 Villeurbanne, France
[3] Rice Univ, Dept Chem, Houston, TX 77005 USA
关键词
D O I
10.1021/ol015526i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The total synthesis of FR901483, a structurally novel immunosuppressant, has been accomplished by the use of technology recently developed in this laboratory for the oxidative cyclization of phenolic oxazolines to spirolactams. Our approach may reflect the biosynthetic pathway leading to the natural product.
引用
收藏
页码:765 / 767
页数:3
相关论文
共 34 条
[1]   BETA-KETONITRILE-DERIVED PROTECTING GROUPS OF THE AMINO FUNCTION - SYNTHESIS OF AMINO-ALCOHOLS [J].
ABARBRI, M ;
GUIGNARD, A ;
LAMANT, M .
HELVETICA CHIMICA ACTA, 1995, 78 (01) :109-121
[2]   Synthesis and biological evaluation of a conformationally free seco-analogue of the immunosuppressant FR901483 [J].
Bonjoch, J ;
Diaba, F ;
Puigbó, G ;
Solé, D ;
Segarra, V ;
Santamaría, L ;
Beleta, J ;
Ryder, H ;
Palacios, JM .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (12) :2891-2897
[3]   Hypervalent iodine oxidation of indolic 2-oxazolines [J].
Braun, NA ;
Bray, JD ;
Ciufolini, MA .
TETRAHEDRON LETTERS, 1999, 40 (27) :4985-4988
[4]   New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building blocks [J].
Braun, NA ;
Ousmer, M ;
Bray, JD ;
Bouchu, D ;
Peters, K ;
Peters, EM ;
Ciufolini, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4397-4408
[5]   Synthesis of spirolactams from tyrosine amides and related substances [J].
Braun, NA ;
Ciufolini, MA ;
Peters, K ;
Peters, EM .
TETRAHEDRON LETTERS, 1998, 39 (26) :4667-4670
[7]   TOTAL SYNTHESIS OF (+/-)-OVALICIN [J].
COREY, EJ ;
DITTAMI, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (01) :256-257
[8]   Synthesis of the functionalized tricyclic core of lactonamycin by oxidative dearomatization [J].
Cox, C ;
Danishefsky, SJ .
ORGANIC LETTERS, 2000, 2 (22) :3493-3496
[9]  
DREEF CE, 1988, RECL TRAV CHIM PAY B, V107, P395
[10]   Optical-active N-monomethyl-derivative from alanine, leucine phenyl-alanine and tyrosine. [J].
Fischer, E ;
Lipschitz, W .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1915, 48 :360-378