1ST SYNTHESIS OF THE DIFURANSESQUITERPENE ATHANASIN AND THE ELUCIDATION OF ITS RELATIVE AND ABSOLUTE-CONFIGURATION

被引：8

作者：

BOJACK, G ^{[1
]}

BORNOWSKI, H ^{[1
]}

机构：

[1] TECH UNIV BERLIN,INST ORGAN CHEM,STR 17 JUNI 135,W-1000 BERLIN 12,GERMANY

来源：

TETRAHEDRON | 1991年 / 47卷 / 44期

关键词：

DIFURANSESQUITERPENE; NATURAL PRODUCT SYNTHESIS; SPECIAL FURAN BUILDING BLOCKS; RELATIVE AND ABSOLUTE CONFIGURATION; OPTICAL ROTATIONS;

D O I：

10.1016/S0040-4020(01)96205-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the naturally occurring difuransesquiterpene athanasin is described. Employing Seebach's method of ''self-reproduction of chirality'', the chiral oxirane 6 is built up, which is successively connected with suitable furan building blocks. Cyclization of the resulting diols 14 a/b gives the enantiomerically pure diastereomers 1a and 1b. Comparison of their spectroscopic data with athanasin after separation allows the elucidation of the natural product's relative and absolute configuration.

引用

页码：9179 / 9186

页数：8

共 12 条

[1] NEW ASPECTS IN THE SYNTHESIS OF MONOALKYLFURANS AND DIALKYLFURANS [J].

BOCK, I ;

BORNOWSKI, H ;

RANFT, A ;

THEIS, H .

TETRAHEDRON, 1990, 46 (04) :1199-1210

[2] NATURALLY OCCURRING TERPENE DERIVATIVES, .30. NEW FURAN-SESQUITERPENE FROM STILPNOPHYTUM-LINIFOLIUM (THUNB) LESS [J].

BOHLMANN, F ;

ZDERO, C .

CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (04) :1071-1073

[3] NATURALLY OCCURRING TERPENE DERIVATIVES .137. NEW FURANOSESQUITERPENES FROM EUMORPHIA SPECIES [J].

BOHLMANN, F ;

ZDERO, C .

PHYTOCHEMISTRY, 1978, 17 (07) :1155-1159

[4]

BOHLMANN F, 1972, Tetrahedron Letters, V11, P1039

[5]

CANNON GW, 1963, ORG SYNTH C, V6, P597

[6] THE REDUCTION OF SUBSTITUTED 2,8-DIOXABICYCLO[3,2,1]OCT-3-YLMETHYL METHANESULFONATES WITH LITHIUM ALUMINUM-HYDRIDE [J].

DIMITRIADIS, E ;

MASSYWESTROPP, RA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (09) :1895-1902

[7]

JULIA M, 1960, B SOC CHIM FR, P1072

[8]

KREISER W, 1981, NACHR CHEM TECH LAB, V29, P370

[9] ALPHA-ALKYLATION OF ALPHA-HETEROSUBSTITUTED CARBOXYLIC-ACIDS WITHOUT RACEMIZATION - EPC-SYNTHESES OF TERTIARY ALCOHOLS AND THIOLS [J].

SEEBACH, D ;

NAEF, R ;

CALDERARI, G .

TETRAHEDRON, 1984, 40 (08) :1313-1324

[10]

SEEBACH D, 1983, LIEBIGS ANN CHEM, P1930

← 1 2 →