SYNTHESIS OF FURANOID TERPENES VIA AN EFFICIENT PALLADIUM-CATALYZED CYCLIZATION OF 4,6-DIENOLS

被引：44

作者：

ANDERSSON, PG ^{[1
]}

BACKVALL, JE ^{[1
]}

机构：

[1] UNIV UPPSALA,DEPT ORGAN CHEM,BOX 531,S-75121 UPPSALA,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 18期

关键词：

D O I：

10.1021/jo00018a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described. The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively. The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

引用

页码：5349 / 5353

页数：5

共 22 条

[1] AKERMARK B, 1987, ORGANOMETALLICS, V6, P620
[2] AKERMARK B, 1987, J ORGANOMET CHEM, V335, P133
[3] ANDERSSON PO, UNPUB
[4] BABLER JH, 1974, TETRAHEDRON LETT, V15, P351
[5] IMPROVED PALLADIUM-CATALYZED 1,4-HALOACYLOXYLATION AND 1,4-DIACYLOXYLATION OF CYCLIC CONJUGATED DIENES
BACKVALL, JE
GRANBERG, KL
HOPKINS, RB
[J]. ACTA CHEMICA SCANDINAVICA, 1990, 44 (05): : 492 - 499
[6] BACKVALL JE, 1991, J ORG CHEM, V56, P2274
[7] BACKVALL JE, 1984, J ORG CHEM, V49, P4619
[8] STEREOCONTROLLED LACTONIZATION REACTIONS VIA PALLADIUM-CATALYSIS
BACKVALL, JE
ANDERSSON, PG
VAGBERG, JO
[J]. TETRAHEDRON LETTERS, 1989, 30 (01) : 137 - 140
[9] STUDIES IN MOLECULAR REARRANGEMENT .4. ALKENYLATION BY USE OF LITHIUM ALKENYLS .2. THE CONDENSATION OF ISOBUTENYL-LITHIUM WITH ACRALDEHYDE AND CROTONALDEHYDE, AND THE OXOTROPIC REARRANGEMENT OF THE RESULTING CARBINOLS
BRAUDE, EA
TIMMONS, CJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1950, (AUG): : 2007 - 2011
[10] SYNTHESIS OF OCIMENOL AND RELATED COMPOUNDS FROM 5-CHLORO-2-PENTANONE
KISE, H
SATO, T
YASUOKA, T
SENO, M
ASAHARA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) : 4454 - 4456

← 1 2 3 →