The first enantiocontrolled synthesis of naturally occurring polyoxygenated cyclohexenylmethanol dibenzoates (-)-zeylenol, (-)-uvarigranol G, (-)-tonkinenin A and (+)-pipoxide

被引:21
作者
Hiroya, K [1 ]
Ogasawara, K [1 ]
机构
[1] Tohoku Univ, Inst Pharmaceut, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1039/a905631i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first enanticontrolled synthesis of five naturally occurring polyoxygenated cyclohexenylmethanol dibenzoates has been achieved to confirm three [(-)-zeylenol, (-)-uvarigranol G, (+)-pipoxide], revise one [(-)-tonkinenin A] and disprove one [(-)-epizeylenol] of the proposed structures.
引用
收藏
页码:2197 / 2198
页数:2
相关论文
共 17 条
[1]   LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].
GEMAL, AL ;
LUCHE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459
[2]   A concise enantio- and diastereo-controlled synthesis of (-)-quinic acid and (-)-shikimic acid [J].
Hiroya, K ;
Ogasawara, K .
CHEMICAL COMMUNICATIONS, 1998, (18) :2033-2034
[3]   ASYMMETRIZATION OF MESO 1,4-ENEDIOL ETHERS BY ISOMERIZATION WITH A CHIRAL BINAP-RH-I CATALYST [J].
HIROYA, K ;
KURIHARA, Y ;
OGASAWARA, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (20) :2287-2289
[4]  
HOLBERT GW, 1979, TETRAHEDRON LETT, P715
[5]   Progress in the Mitsunobu reaction. A review [J].
Hughes, DL .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1996, 28 (02) :127-164
[6]   STRUCTURES OF ZEYLENOL AND ZEYLENA, CONSTITUENTS OF UVARIA-ZEYLANICA (ANNONACEAE) [J].
JOLAD, SD ;
HOFFMANN, JJ ;
SCHRAM, KH ;
COLE, JR ;
TEMPESTA, MS ;
BATES, RB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (21) :4267-4272
[7]   1-EPIZEYLENOL FROM UVARIA-ZEYLANICA ROOTS [J].
JOLAD, SD ;
HOFFMANN, JJ ;
COLE, JR ;
TEMPESTA, MS ;
BATES, RB .
PHYTOCHEMISTRY, 1984, 23 (04) :935-936
[8]  
Konno H, 1999, SYNTHESIS-STUTTGART, P1135
[9]   ALKYLSILYL CYANIDES AS SILYLATING AGENTS [J].
MAI, K ;
PATIL, G .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (18) :3545-3548
[10]  
MITSUNOBU O, 1992, ORG REACTIONS, V42, P335