REACTION OF PODOCARPA-6,8,11,13-TETRAENES WITH META-CHLOROPERBENZOIC ACID AND WITH DIMETHYLDIOXIRAN - SYNTHESIS OF METHYL 6-ALPHA,7-ALPHA-EPOXY-12-METHOXY-PODOCARPA-8,11,13-TRIEN-19-OATE

被引：10

作者：

CAMBIE, RC

GRIMSDALE, AC

RUTLEDGE, PS

WALKER, MF

WOODGATE, PD

机构：

[1] University of Auckland, Auckland

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1991年 / 44卷 / 11期

关键词：

D O I：

10.1071/CH9911553

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of some podocarpa-6,8,11,13-tetraenes with m-chloroperbenzoic acid in either a one-phase system or a two-phase system with an aqueous buffer leads to epoxide-opened products. Successful epoxidations have been achieved in high yield by using the neutral oxidant dimethyldioxiran. The hydroboration-oxidation of methyl 12-benzyloxypodocarpa-6,8,11,13-tetraen-19-oate has been examined.

引用

页码：1553 / 1573

页数：21

共 30 条

[1] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[2] AKHREM AA, 1968, RUSS CHEM REV, V37, P448
[3] STUDIES ON INTRAMOLECULAR ALKYLATION .3. PREPARATION OF GAMMA-LACTAMS FROM PODOCARPIC ACID - MODELS FOR DITERPENE ALKALOID SYNTHESIS
BALGIR, BS
MANDER, LN
PRAGER, RH
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (06) : 1245 - 1256
[4] CHEMISTRY OF PODOCARPACEAE .19. OXIDATION OF SOME PODOCARPA-8,11,13-TRIEN-19-OIC ACID DERIVATIVES WITH LEAD TETRAACETATE
BENNETT, CR
CAMBIE, RC
DENNY, WA
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (05) : 1069 - &
[5] CHEMISTRY OF PODOCARPACEAE .12. OXIDATION OF O-METHYLPODOCARPIC ACID WITH LEAD TETRA-ACETATE
BENNETT, CR
CAMBIE, RC
[J]. TETRAHEDRON, 1967, 23 (02) : 927 - &
[6] BIEG T, 1985, SYNTHESIS-STUTTGART, P76
[7] SESQUITERPENOIDS OF WARBURGIA SPECIES .2. UGANDENSOLIDE AND UGANDENSIDIAL (CINNAMODIAL)
BROOKS, CJW
DRAFFAN, GH
[J]. TETRAHEDRON, 1969, 25 (14) : 2887 - &
[8] HYDROBORATION .24. DIRECTIVE EFFECTS IN HYDROBORATION OF SOME SUBSTITUTED STYRENES
BROWN, HC
SHARP, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (24) : 5851 - &
[9] USE OF DIMETHYLDIOXIRANE IN THE PREPARATION OF HIGHLY REACTIVE COMPOUNDS - 1ST DIRECT EPOXIDATION OF PRECOCENES
BUJONS, J
CAMPS, F
MESSEGUER, A
[J]. TETRAHEDRON LETTERS, 1990, 31 (36) : 5235 - 5236
[10] THE INTRODUCTION OF OXYGEN FUNCTIONS INTO THE B-RING IN SYNTHETIC DITERPENES
BURNELL, RH
JEAN, M
[J]. SYNTHETIC COMMUNICATIONS, 1984, 14 (13) : 1229 - 1237

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