Studies toward the synthesis of vinigrol. First construction of the tricyclic ring system

被引：33

作者：

Devaux, JF ^{[1
]}

Hanna, I ^{[1
]}

Lallemand, JY ^{[1
]}

机构：

[1] ECOLE POLYTECH,CNRS,ORGAN SYNTH LAB,F-91128 PALAISEAU,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 15期

关键词：

D O I：

10.1021/jo970343o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of a functionalized tricyclic skeleton of vinigrol is described. The key step involved an anionic oxy-Cope rearrangement of bicyclic allylic alcohol 18, readily prepared by highly stereoselective addition of vinyl magnesium chloride to the hydroxy enone 15b. Introduction of the tertiary hydroxy group at carbon 8a was achieved by an unexpected hydration of 30 with aqueous trifluoroacetic acid.

引用

页码：5062 / 5068

页数：7

共 30 条

[1] AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF BICYCLO[2.2.2]OCTANE-2,6-DIONE
ALMQVIST, F
EKLUND, L
FREJD, T
[J]. SYNTHETIC COMMUNICATIONS, 1993, 23 (11) : 1499 - 1505
[2] VINIGROL, A NOVEL ANTIHYPERTENSIVE AND PLATELET-AGGREGATION INHIBITORY AGENT PRODUCED BY A FUNGUS, VIRGARIA-NIGRA .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL AND BIOLOGICAL PROPERTIES
ANDO, T
TSURUMI, Y
OHATA, N
UCHIDA, I
YOSHIDA, K
OKUHARA, M
[J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (01) : 25 - 30
[3] VINIGROL, A NOVEL ANTIHYPERTENSIVE AND PLATELET-AGGREGATION INHIBITORY AGENT PRODUCED BY A FUNGUS, VIRGARIA-NIGRA .2. PHARMACOLOGICAL CHARACTERISTICS
ANDO, T
YOSHIDA, K
OKUHARA, M
[J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (01) : 31 - 35
[4] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS
BARTON, DHR
MCCOMBIE, SW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16): : 1574 - 1585
[5] SYNTHETIC STUDIES DIRECTED TOWARD NATURALLY-OCCURRING CYCLOOCTANOIDS .2. A STEREOCONTROLLED ASSEMBLY OF (+/-)-PLEUROMUTILIN VIA A REMARKABLE STERICALLY DEMANDING OXY-COPE REARRANGEMENT
BOECKMAN, RK
SPRINGER, DM
ALESSI, TR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) : 8284 - 8286
[6] INTRAMOLECULAR REARRANGEMENTS - EPIMERIZATION OF BICYCLIC VINYL TERTIARY ALCOHOLS VIA A [2,3] SULFOXIDE SIGMATROPIC REARRANGEMENT
BROWN, WL
FALLIS, AG
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1987, 65 (08) : 1828 - 1832
[7] CRABTREE SR, 1990, SYNLETT, P169
[8] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7277 - 7287
[9] Devaux JF, 1996, J CHEM RES-S, P32
[10] Unexpected effect of an hydroxyl group on pi-facial selectivity in the nucleophilic addition to bicyclo[2.2.2]octan-2-ones
Devaux, JF
Fraisse, P
Hanna, I
Lallemand, JY
[J]. TETRAHEDRON LETTERS, 1995, 36 (52) : 9471 - 9474

← 1 2 3 →