A SHORT SYNTHESIS OF THE TRICYCLIC RING-SYSTEM OF VINIGROL

被引:41
作者
DEVAUX, JF
HANNA, I
LALLEMAND, JY
机构
[1] ECOLE POLYTECH,CNRS,SYNTHESE ORGAN LAB,F-91128 PALAISEAU,FRANCE
[2] CNRS,CHIM STRUCT BIOMOLEC LAB,F-93012 BOBIGNY,FRANCE
关键词
D O I
10.1021/jo00061a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of the decahydro-1,5-butanonaphthalene skeleton of vinigrol is described which features as the key step by anionic oxy-Cope rearrangement.
引用
收藏
页码:2349 / 2350
页数:2
相关论文
共 14 条
[1]   VINIGROL, A NOVEL ANTIHYPERTENSIVE AND PLATELET-AGGREGATION INHIBITORY AGENT PRODUCED BY A FUNGUS, VIRGARIA-NIGRA .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES [J].
ANDO, T ;
TSURUMI, Y ;
OHATA, N ;
UCHIDA, I ;
YOSHIDA, K ;
OKUHARA, M .
JOURNAL OF ANTIBIOTICS, 1988, 41 (01) :25-30
[2]   VINIGROL, A NOVEL ANTIHYPERTENSIVE AND PLATELET-AGGREGATION INHIBITORY AGENT PRODUCED BY A FUNGUS, VIRGARIA-NIGRA .2. PHARMACOLOGICAL CHARACTERISTICS [J].
ANDO, T ;
YOSHIDA, K ;
OKUHARA, M .
JOURNAL OF ANTIBIOTICS, 1988, 41 (01) :31-35
[3]   SYNTHETIC STUDIES DIRECTED TOWARD NATURALLY-OCCURRING CYCLOOCTANOIDS .2. A STEREOCONTROLLED ASSEMBLY OF (+/-)-PLEUROMUTILIN VIA A REMARKABLE STERICALLY DEMANDING OXY-COPE REARRANGEMENT [J].
BOECKMAN, RK ;
SPRINGER, DM ;
ALESSI, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8284-8286
[4]   INTRAMOLECULAR REARRANGEMENTS - EPIMERIZATION OF BICYCLIC VINYL TERTIARY ALCOHOLS VIA A [2,3] SULFOXIDE SIGMATROPIC REARRANGEMENT [J].
BROWN, WL ;
FALLIS, AG .
CANADIAN JOURNAL OF CHEMISTRY, 1987, 65 (08) :1828-1832
[5]   LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].
GEMAL, AL ;
LUCHE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459
[6]   CHEMISTRY OF BENZOQUINONES AND MASKED BENZOQUINONES .11. DIELS-ALDER REACTIONS OF 8-TRIMETHYLSILYLOXY-1,4-DIOXASPIRO[4,5]DECA-6,8-DIENE [J].
HUNG, SC ;
LIAO, CC .
TETRAHEDRON LETTERS, 1991, 32 (32) :4011-4014
[7]   ALKOXIDE-ACCELERATED SIGMATROPIC REARRANGEMENTS - A NOVEL ENTRY TO THE BICYCLO[5.3.1]UNDEC-7-ENE SYSTEM OF THE TAXANE DITERPENES [J].
MARTIN, SF ;
WHITE, JB ;
WAGNER, R .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (16) :3190-3192
[8]   PREPARATIVE AND STEREOCHEMICAL FEATURES OF THE SULFOXIDE-SULFENATE [2,3] SIGMATROPIC REARRANGEMENT IN 17-VINYL-17-HYDROXY STEROIDS [J].
MORERA, E ;
ORTAR, G .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01) :119-121
[9]  
NORRIS DB, Patent No. 9107953
[10]   COMPARATIVE-ANALYSIS OF MOLECULAR-RECOGNITION LEVELS ATTAINED DURING CAPTURE OF CHIRAL CYCLOPENTENYL ORGANOMETALLICS BY CONFORMATIONALLY IMMOBILIZED KETONIC SYSTEMS [J].
PAQUETTE, LA ;
HE, W ;
ROGERS, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2291-2300