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
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.
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页码:3431 / 3434
页数:4
相关论文
共 36 条
[11]   APPROACH TO THE TOTAL SYNTHESIS OF CHLOROTHRICOLIDE - SYNTHESIS OF (+/-)-19,20-DIHYDRO-24-O-METHYLCHLOROTHRICOLIDE, METHYL-ESTER, ETHYL CARBONATE [J].
IRELAND, RE ;
VARNEY, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (05) :635-648
[12]   METABOLIC PRODUCTS OF MICROORGANISMS .73. CHLOROTHRICIN AND DECHLOROTHRICIN [J].
KELLERSC.W ;
MUNTWYLER, R ;
PACHE, W ;
ZAHNER, H .
HELVETICA CHIMICA ACTA, 1969, 52 (01) :127-+
[13]   HYDROLYSIS OF ACETALS AND KETALS USING LIBF4 [J].
LIPSHUTZ, BH ;
HARVEY, DF .
SYNTHETIC COMMUNICATIONS, 1982, 12 (04) :267-277
[14]   KIJANIMICIN .2. STRUCTURE AND ABSOLUTE STEREOCHEMISTRY OF KIJANIMICIN [J].
MALLAMS, AK ;
PUAR, MS ;
ROSSMAN, RR ;
MCPHAIL, AT ;
MACFARLANE, RD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) :3940-3943
[15]   KIJANIMICIN .1. STRUCTURES OF THE INDIVIDUAL SUGAR COMPONENTS [J].
MALLAMS, AK ;
PUAR, MS ;
ROSSMAN, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) :3938-3940
[16]   KIJANIMICIN .3. STRUCTURE AND ABSOLUTE STEREOCHEMISTRY OF KIJANIMICIN [J].
MALLAMS, AK ;
PUAR, MS ;
ROSSMAN, RR ;
MCPHAIL, AT ;
MACFARLANE, RD ;
STEPHENS, RL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (07) :1497-1534
[17]   CONJUGATE ADDITION OF ORGANOCUPRATES TO TRANS-4A,5,6,7,8,8A-HEXAHYDRONAPHTHALENE-1-CARBOXALDEHYDES - SYNTHESIS OF A CHLOROTHRICIN DEGRADATION PRODUCT [J].
MARSHALL, JA ;
AUDIA, JE ;
SHEARER, BG .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10) :1730-1735
[18]   ACYCLIC STEREOCONTROL IN CATALYZED INTRAMOLECULAR DIELS-ALDER CYCLIZATIONS LEADING TO OCTAHYDRONAPHTHALENECARBOXALDEHYDES [J].
MARSHALL, JA ;
GROTE, J ;
AUDIA, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1186-1194
[19]  
MARSHALL JA, 1984, J ORG CHEM, V49, P5279
[20]   METABOLITES OF MICROORGANISMS .84. SYNTHESIS OF 5-CHLORO-6-METHYL-SALICYLIC ACID METHYL ETHER, ANABOLITE OF CHLOROTHRICIN [J].
MUNTWYLER, R ;
WIDMER, J ;
KELLERSC.W .
HELVETICA CHIMICA ACTA, 1970, 53 (06) :1544-+