AMIDE ACETAL CLAISEN REARRANGEMENT IN THE SYNTHESIS OF MESEMBRANE ALKALOIDS

被引：8

作者：

BAUERMEISTER, S ^{[1
]}

GOUWS, ID ^{[1
]}

STRAUSS, HF ^{[1
]}

VENTER, EMM ^{[1
]}

机构：

[1] UNIV PRETORIA,DEPT CHEM,PRETORIA 0002,SOUTH AFRICA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 03期

关键词：

D O I：

10.1039/p19910000561

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of primary and secondary allylic alcohols (differing in the degree of steric hindrance and of amide acetals (achiral and chiral) is reported. These compounds were used as substrates in the amide acetal Claisen rearrangement, and the effect of Lewis acids on the stereoselectivity of the reaction was studied. The rearrangement products have been applied to the synthesis of the mesembrane alkaloids (-)-mesembranone, rac-Omicron-methylijoubertiamine and joubertiamine.

引用

页码：561 / 565

页数：5

共 19 条

[1] BENNETT GB, 1977, SYNTHESIS-STUTTGART, P589
[2] REARRANGEMENT OF ALLYL ARYL ETHERS ALD ALLYL CYCLOHEXADIENONES USING BORON TRICHLORIDE
BORGULYA, J
MADEJA, R
FAHRNI, P
HANSEN, HJ
SCHMID, H
BARNER, R
[J]. HELVETICA CHIMICA ACTA, 1973, 56 (01) : 14 - 75
[3] CHEMISTRY OF OXAZIRIDINES .2. IMPROVED SYNTHESIS OF 2-SULFONYLOXAZIRIDINES
DAVIS, FA
STRINGER, OD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (09) : 1774 - 1775
[4] SYNTHESIS OF ALPHA-HYDROXY CARBONYL-COMPOUNDS (ACYLOINS) - DIRECT OXIDATION OF ENOLATES USING 2-SULFONYLOXAZIRIDINES
DAVIS, FA
VISHWAKARMA, LC
BILLMERS, JM
FINN, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) : 3241 - 3243
[5] ESCHENMOSER A, 1964, HELV CHIM ACTA, V47, P2425
[6] ESCHENMOSER A, 1969, HELV CHIM ACTA, V52, P1030
[7] STEREOCHEMISTRY OF SIGMATROPIC[3,3]-REARRANGEMENT AND SIGMATROPIC[5,5]-REARRANGEMENT
HANSEN, HJ
SCHMID, H
[J]. TETRAHEDRON, 1974, 30 (13) : 1959 - 1969
[8] ASYMMETRIC INDUCTION IN THERMAL REACTIONS OF ALLYLIC ALCOHOLS WITH N,N-DIMETHYLACETAMIDE DIMETHYL ACETAL AND TRIETHYL ORTHOACETATE
HILL, RK
SOMAN, R
SAWADA, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (23) : 3737 - &
[9] ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION
IRELAND, RE
MUELLER, RH
WILLARD, AK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) : 2868 - 2877
[10] JACKMAN LM, 1969, NUCL MAGN RESON, P361

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