Facile construction and divergent transformation of polycyclic isoxazoles: Direct access to polyketide architectures

被引:52
作者
Bode, JW
Hachisu, Y
Matsuura, T
Suzuki, K [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan
[2] Japan Sci & Technol Corp, CREST, Meguro Ku, Tokyo 1528551, Japan
关键词
D O I
10.1021/ol027283f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Base-promoted cyclocondensation of C-chloro oximes with cyclic 1,3-diketones affords functionalized isoxazoles in good yield and under convenient reaction conditions. This process enables the synthesis of highly substituted products with notable functional group tolerance. The products obtained are directly converted to a variety of polyketide-derived polycyclic structures including xanthenes, anthracenes, and benzophenones.
引用
收藏
页码:391 / 394
页数:4
相关论文
共 11 条
[1]   CONVENIENT ONE-STEP SYNTHESIS OF TETRAHYDROBENZISOXAZOLES VIA 1,3-CYCLOADDITION OF NITRILE OXIDES TO CYCLOHEXANE-1,3-DIONE DERIVATIVES [J].
AKHREM, AA ;
LAKHVICH, FA ;
KHRIPACH, VA ;
POZDEYEV, AG .
SYNTHESIS-STUTTGART, 1978, (01) :43-43
[2]  
[Anonymous], 1979, ADV HETEROCYCL CHEM
[3]   Isoxazole→benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles [J].
Bode, JW ;
Uesuka, H ;
Suzuki, K .
ORGANIC LETTERS, 2003, 5 (04) :395-398
[4]  
BODE JW, UNPUB
[5]  
DALPIAZ V, 1975, SYNTHESIS-STUTTGART, P664
[6]   SYNTHESIS AND ANTICONVULSANT ACTIVITY OF ENAMINONES [J].
EDAFIOGHO, IO ;
HINKO, CN ;
CHANG, HJ ;
MOORE, JA ;
MULZAC, D ;
NICHOLSON, JM ;
SCOTT, KR .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (15) :2798-2805
[7]   Modification of post-PKS tailoring steps through combinatorial biosynthesis [J].
Rix, U ;
Fischer, C ;
Remsing, LL ;
Rohr, J .
NATURAL PRODUCT REPORTS, 2002, 19 (05) :542-580
[8]   Chemistry of 2-acylcycloalkane-1,3-diones [J].
Rubinov, DB ;
Rubinova, IL ;
Akhrem, AA .
CHEMICAL REVIEWS, 1999, 99 (04) :1047-1065
[9]   Polyketide biosynthesis: a millennium review [J].
Staunton, J ;
Weissman, KJ .
NATURAL PRODUCT REPORTS, 2001, 18 (04) :380-416
[10]   REACTIONS OF TRIFLUOROACETONITRILE OXIDE OR TRIFLUOROACETONITRILIMINES WITH BETA-DIKETONES AND BETA-KETO-ESTERS [J].
TANAKA, K ;
KISHIDA, M ;
MAENO, S ;
MITSUHASHI, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (08) :2631-2632