STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF TETRONOLIDE .2. A STEREOSELECTIVE ROUTE TO THE RACEMIC CYCLOHEXENE SUBUNIT

被引:28
作者
BOECKMAN, RK
ESTEP, KG
NELSON, SG
WALTERS, MA
机构
[1] Department of Chemistry University of Rochester, Rochester
关键词
D O I
10.1016/S0040-4039(00)79872-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short stereoselective sequence is described for the preparation of the racemic form of the highly functionalized cyclohexene derivative 2 which comprises the upper segment of tetronolide (1), the aglycone of the antitumor tetrocarcins. A key element of this route is the rapid assembly and intramolecular cycloaddition of the trienyl enol pyruvate 4, which achieves complete control over regiochemistry and good stereochemical control.
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页码:4095 / 4098
页数:4
相关论文
共 16 条
[1]   STEREOCONTROL IN THE INTRAMOLECULAR DIELS-ALDER REACTION .6. USE OF MIXED ACETALS AS ESTER EQUIVALENTS IN THE CONNECTING CHAIN [J].
BOECKMAN, RK ;
FLANN, CJ .
TETRAHEDRON LETTERS, 1983, 24 (46) :5035-5038
[2]  
BOECKMAN RK, 1991, TETRAHEDRON LETT, V32
[3]  
BOECKMAN RK, 1991, UNPUB
[4]   NUCLEAR ANALOGS OF BETA-LACTAM ANTIBIOTICS .2. TOTAL SYNTHESIS OF 8-OXO-4-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACIDS [J].
BRYAN, DB ;
HALL, RF ;
HOLDEN, KG ;
HUFFMAN, WF ;
GLEASON, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (07) :2353-2355
[5]   REDUCTION OF BETA-HALO-ALPHA,BETA-UNSATURATED KETONES [J].
CLARK, RD ;
HEATHCOC.CH .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (20) :3658-3658
[6]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[7]   REFORMATSKY REACTION .1. PREPARATION AND REACTIVITY OF ORGANOZINC COMPOUNDS DERIVED FROM VARIOUS ALCOHOL CROTONATES [J].
COUFFIGN.R ;
GAUDEMAR, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 60 (02) :209-217
[8]  
ESTEP KG, 1987, THESIS U ROCHESTER
[9]  
ISHIZUMI K, 1968, CHEM PHARM BULL, V16, P492
[10]   METHYL ALPHA-ACYLOXY-GAMMA-METHYLENE-BETA-TETRONATE - PREPARATION AND USE AS A BUILDING BLOCK FOR THE SYNTHESIS OF THE SPIROTETRONIC ACID STRUCTURE OF CHLOROTHRICOLIDE [J].
OKUMURA, K ;
OKAZAKI, K ;
TAKEDA, K ;
YOSHII, E .
TETRAHEDRON LETTERS, 1989, 30 (17) :2233-2236