STEREOSELECTIVE SYNTHESIS OF PRECURSORS OF NATURALLY-OCCURRING ROBUSTADIALS-A AND ROBUSTADIALS-B

被引:27
作者
KOSER, S
HOFFMANN, HMR
WILLIAMS, DJ
机构
[1] UNIV HANNOVER,DEPT ORGAN CHEM,SCHNEIDERBERG 1 B,D-30167 HANNOVER,GERMANY
[2] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,CHEM CRYSTALLOGR LAB,LONDON SW7 2AY,ENGLAND
关键词
D O I
10.1021/jo00075a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The key intermediates of robustadials A and B have been synthesized in a new and stereoselective synthesis with high overall yields starting from (S)-(-)-beta-pinene and readily available materials; after bromination of one stereoisomer the absolute configuration was established by X-ray diffraction analysis.
引用
收藏
页码:6163 / 6165
页数:3
相关论文
共 24 条
[1]   A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].
ADAM, W ;
BIALAS, J ;
HADJIARAPOGLOU, L .
CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377
[2]  
[Anonymous], 1993, ANGEW CHEM, DOI 10.1002/ange.19931050204
[3]   SILYLATION-MEDIATED OXIDATION OF 4-AZA-3-KETOSTEROIDS WITH DDQ PROCEEDS VIA DDQ-SUBSTRATE ADDUCTS [J].
BHATTACHARYA, A ;
DIMICHELE, LM ;
DOLLING, UH ;
DOUGLAS, AW ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) :3318-3319
[4]  
BLANCO L, 1976, SYNTHESIS-STUTTGART, P194
[5]  
Boger D. L., 1987, HETERO DIELS ALDER M
[6]   FURTHER OBSERVATIONS ON THE LEWIS ACID-CATALYZED BENZYLIC HYDROPEROXIDE REARRANGEMENT - USE OF A BORON-TRIFLUORIDE HYDROGEN-PEROXIDE PREFORMED, AGED REAGENT [J].
BOGER, DL ;
COLEMAN, RS .
TETRAHEDRON LETTERS, 1987, 28 (10) :1027-1030
[7]   2 CONVENIENT METHODS FOR THE GENERATION OF METHYLENE MELDRUMS ACID FOR DIELS-ALDER REACTIONS [J].
BUZINKAI, JF ;
HRUBOWCHAK, DM ;
SMITH, FX .
TETRAHEDRON LETTERS, 1985, 26 (27) :3195-3198
[8]   REVISED STRUCTURES OF ROBUSTADIALS A AND B FROM EUCALYPTUS-ROBUSTA [J].
CHENG, Q ;
SNYDER, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4562-4567
[9]   A NEW SYNTHESIS OF FUNCTIONALIZED 6,8-DIOXABICYCLO[3.2.1]OCTANES [J].
DAUDE, N ;
EGGERT, U ;
HOFFMANN, HMR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (03) :206-207
[10]  
Ho T.-L., 1992, TANDEM ORGANIC REACT