SYNTHESIS AND REARRANGEMENT OF METHYL 8,14-BETA-EPOXYPIMARATE FOR A CASSANE DITERPENE SKELETON

被引：6

作者：

SAM, N

SANMIGUEL, BA

TARAN, M

DELMOND, B

机构：

[1] UNIV BORDEAUX 1,INST PIN,351 COURS LIBERAT,F-33405 TALENCE,FRANCE

[2] UNIV BORDEAUX 1,CHIM ORGAN & ORGANOMET LAB,CNRS,UA 35,F-33405 TALENCE,FRANCE

[3] UNIV BORDEAUX 2,UER SCI PHARMACEUT,F-33076 BORDEAUX,FRANCE

来源：

TETRAHEDRON | 1991年 / 47卷 / 44期

关键词：

D O I：

10.1016/S0040-4020(01)96206-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl-8,14-beta-epoxypimarate is stereoselectively obtained from pimaric acid via a stereocontrolled epoxidation of methyl-15 hydroxy-16-nor pimarate. The isomerisation of this epoxide with Lewis acid and on silica gel has established the existence of new rearrangements of the diterpene skeleton leading to bicyclic diterpene compounds by a Grob fragmentation and to one cycloditerpene compound.

引用

页码：9187 / 9194

页数：8

共 20 条

[1] [Anonymous], 1972, ORG SYNTH
[2] APSIMON JW, 1974, CAN J CHEM, V56, P2156
[3] ARREGUYSANMIGUEL B, 1990, SYNTHETIC COMMUN, V20, P719
[4] STEREOCHEMISTRY OF FURANODITERPENOIDS ALPHA-CAESALPIN, BETA-CAESPALPIN AND DELTA-CAESALPIN
BALMAIN, A
CONNOLLY, JD
FERRARI, M
GHISALBE.EL
PAGNONI, UM
PELIZZON.F
[J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (19): : 1244 - &
[5] CECCHERELLI P, 1978, GAZZ CHIM ITAL, V108, P129
[6] C-13 NMR-STUDY OF EPOXIDES IN THE DITERPENE SERIES
DELMOND, B
PAPILLAUD, B
VALADE, J
PETRAUD, M
BARBE, B
[J]. ORGANIC MAGNETIC RESONANCE, 1979, 12 (04): : 209 - 211
[7] HUMBER LG, 1955, J CHEM SOC, P1044
[8] PIMARANE -] CASSANE REARRANGEMENT - SYNTHESIS OF A POTENTIAL INTERMEDIATE FROM ISOPIMARIC ACID
JOHNSTON, JP
OVERTON, HH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (08): : 853 - 858
[9] KAHN JB, 1955, J PHARMACOL EXP THER, V115, P305
[10] LODER JW, 1975, TETRAHEDRON LETT, P2497

← 1 2 →