STUDIES ON THE TOTAL SYNTHESIS OF STREPTOGRAMIN ANTI-BIOTICS - GRISEOVIRIDIN AND MADUMYCIN (A-2315A)

被引:24
作者
MEYERS, AI
LAWSON, J
AMOS, RA
WALKER, DG
SPOHN, RF
机构
[1] Department of Chemistry, Colorado State University, Fort Collins
基金
美国国家卫生研究院;
关键词
D O I
10.1351/pac198254122537
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convergent synthesis of the macrocyclic anti-biotics Madumycin II (A-2315A) 1 and Griseovi ridi n 2 is in progress. Al 1 of the stereochemical centers and functional groups have been incorporated with the former obtained as pure enantiomers. The routes, pitfalls, and strategy leading to the main synthetic fragments are disclosed. All that remains to complete the synthesis is the joining together of the two major units (5, 6, and 7 ). © 2013, Walter de Gruyter. All rights reserved.
引用
收藏
页码:2537 / 2544
页数:8
相关论文
共 13 条
[1]   STRUCTURE OF ANTIBIOTIC GRISEOVIRIDIN [J].
BIRNBAUM, GI ;
HALL, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (07) :1926-1931
[2]  
CHARNEY J, 1953, ANTIBIOT CHEMOTHER, V3, P1283
[3]   TOTAL SYNTHESIS OF (S)-12-HYDROXY-5,8,14-CIS-10-TRANS-EICOSATETRAENOIC ACID (SAMUELSSONS HETE) [J].
COREY, EJ ;
NIWA, H ;
KNOLLE, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) :1942-1943
[4]   A NEW SYNTHESIS OF OXAZOLES AND IMINAZOLES INCLUDING ITS APPLICATION TO THE PREPARATION OF OXAZOLE [J].
CORNFORTH, JW ;
CORNFORTH, RH .
JOURNAL OF THE CHEMICAL SOCIETY, 1947, (JAN) :96-102
[5]   STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
NELSON, JV ;
VOGEL, E ;
TABER, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111
[6]   GRISEOVIRIDIN [J].
FALLONA, MC ;
STOESSL, A ;
MCMORRIS, TC ;
MAYO, PD ;
MONEY, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (21) :4162-&
[7]   ANOMALOUS METALATION BEHAVIOR IN 1,3-OXAZOLES - ALKYLATION OF 2-METHYL-4-CARBOXYOXAZOLES VIA THE CORNFORTH INTERMEDIATE [J].
MEYERS, AI ;
LAWSON, JP .
TETRAHEDRON LETTERS, 1981, 22 (33) :3163-3166
[8]   HIGHLY STEREOSELECTIVE ROUTE TO (E)-ALLYL AMINES VIA VINYLTRI-N-BUTYLPHOSPHONIUM SALTS (SCHWEIZER REACTION) [J].
MEYERS, AI ;
LAWSON, JP ;
CARVER, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (15) :3119-3123
[9]   STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF STREPTOGRAMIN ANTIBIOTICS - ENANTIOSPECIFIC APPROACH TO THE 9-MEMBERED MACROCYCLE OF GRISEOVIRIDIN [J].
MEYERS, AI ;
AMOS, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :870-872
[10]   CONVENIENT PREPARATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
MEYERS, AI ;
TOMIOKA, K ;
FLEMING, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) :3788-3789