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
[21]   Total synthesis of (±)-TAN1251A [J].
Nagumo, S ;
Nishida, A ;
Yamazaki, C ;
Murashige, K ;
Kawahara, N .
TETRAHEDRON LETTERS, 1998, 39 (25) :4493-4496
[22]  
OUSMER M, UNPUB KRISTALLOGR NC
[23]  
OUSMER M, 2000, KRISTALLOGR NCS, V215, P597
[24]   FR901483, a novel immunosuppressant isolated from Cladobotryum sp No 11231 - Taxonomy of the producing organism, fermentation, isolation, physico-chemical properties and biological activities [J].
Sakamoto, K ;
Tsujii, E ;
Abe, F ;
Nakanishi, T ;
Yamashita, M ;
Shigematsu, N ;
Izumi, S ;
Okuhara, M .
JOURNAL OF ANTIBIOTICS, 1996, 49 (01) :37-44
[25]  
Scheffler G, 2000, ANGEW CHEM INT EDIT, V39, P4593, DOI 10.1002/1521-3773(20001215)39:24<4593::AID-ANIE4593>3.0.CO
[26]  
2-X
[27]  
Shirafuji H., 1991, PCT Int. Appl. WO, Patent No. 9113887
[28]   Total synthesis of (-)-FR901483 [J].
Snider, BB ;
Lin, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (34) :7778-7786
[29]   Biomimetic Total Syntheses of (-)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D [J].
Snider, BB ;
Lin, H .
ORGANIC LETTERS, 2000, 2 (05) :643-646
[30]   HYPERVALENT IODINE OXIDATION OF PARA-ALKOXYPHENOLS AND RELATED-COMPOUNDS - A GENERAL-ROUTE TO PARA-BENZOQUINONE MONOACETALS AND SPIRO LACTONES [J].
TAMURA, Y ;
YAKURA, T ;
HARUTA, J ;
KITA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3927-3930