AN INTRAMOLECULAR DIELS-ALDER APPROACH TO THE SYNTHESIS OF CHLOROTHRICOLIDE - SYNTHESIS OF (+/-)-24-O-METHYLCHLOROTHRICOLIDE

被引：44

作者：

TAKEDA, K

IGARASHI, Y

OKAZAKI, K

YOSHII, E

YAMAGUCHI, K

机构：

[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,SUGITANI 2630,SUGITANI,TOYAMA 93001,JAPAN

[2] SHOWA UNIV,SCH PHARMACEUT SCI,SHINAGAWA KU,TOKYO 142,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 11期

关键词：

D O I：

10.1021/jo00298a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: Cycloaddition of a-(acyloxy)-7-methylene-0-tetronate 16, obtained by condensation of three segments ((±)-ll, 12, and 15), affords four diastereomeric macrolides 17a-d (1:2.8:1.9:0.9 ratio). The exo mode adduct 17a has been converted to (±)-24-0-methylchIorothricolide (19). © 1990, American Chemical Society. All rights reserved.

引用

收藏

页码：3431 / 3434

页数：4

相关论文

共 36 条

[1] STEREOCONTROL IN THE INTRAMOLECULAR DIELS-ALDER REACTION .7. USE OF THE TRIMETHYLSILYL GROUP AS A REMOVABLE STEREOCONTROL ELEMENT TO PROVIDE GREATLY ENHANCED LEVELS OF DIASTEREOSELECTION [J].

BOECKMAN, RK ;

BARTA, TE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (18) :3421-3423

[2] METABOLITES OF MICROORGANISMS .108. CRYSTAL-STRUCTURE ANALYSIS OF CHLOROTHRICOLIDE METHYL-ESTER [J].

BRUFANI, M ;

CERRINI, S ;

MUNTWYLER, R ;

FEDELI, W ;

MAZZA, F .

HELVETICA CHIMICA ACTA, 1972, 55 (06) :2094-+

[3] SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].

DALCANALE, E ;

MONTANARI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569

[4] CYTOCHALASAN SYNTHESIS - TOTAL SYNTHESIS OF CYTOCHALASIN-G [J].

DYKE, H ;

STEEL, PG ;

THOMAS, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (03) :525-528

[5] SYNTHESIS OF THE BOTTOM HALF OF CHLOROTHRICOLIDE [J].

HALL, SE ;

ROUSH, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4611-4621

[6]

HASSNER A, 1978, TETRAHEDRON LETT, P4475

[7] THE STRUCTURE OF TETRONOLIDE, THE AGLYCONE OF ANTI-TUMOR ANTIBIOTIC TETROCARCIN [J].

HIRAYAMA, N ;

KASAI, M ;

SHIRAHATA, K ;

OHASHI, Y ;

SASADA, Y .

TETRAHEDRON LETTERS, 1980, 21 (26) :2559-2560

[8] APPROACH TO THE TOTAL SYNTHESIS OF CHLOROTHRICOLIDE - SYNTHESIS OF 7-EPI-BOTTOM HALF AND ITS UNION WITH TOP HALF SYSTEMS [J].

IRELAND, RE ;

THOMPSON, WJ ;

SROUJI, GH ;

ETTER, R .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :4863-4873

[9] STEREOCHEMISTRY OF THE DIELS-ALDER REACTION OF VINYLCYCLOHEXENE OR 1-[ALPHA-(TERT-BUTYLDIMETHYLSILYLOXY)VINYL]-DELTA-1-CYCLOHEXENE AND 2-METHYLCYCLOPENTENONE [J].

IRELAND, RE ;

THOMPSON, WJ ;

MANDEL, NS ;

MANDEL, GS .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (20) :3583-3585

[10] APPROACH TO THE TOTAL SYNTHESIS OF CHLOROTHRICOLIDE - SYNTHESIS OF THE TOP HALF [J].

IRELAND, RE ;

THOMPSON, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (17) :3041-3052

← 1 2 3 4 →