THE FIRST EXAMPLE OF ASYMMETRIC DIHYDROXYLATION OF CYCLOPROPYLIDENE DERIVATIVES - AN ENANTIOENRICHED FORMAL TOTAL SYNTHESIS OF (-)-FILIFORMIN

被引:30
作者
NEMOTO, H [1 ]
MIYATA, J [1 ]
HAKAMATA, H [1 ]
FUKUMOTO, K [1 ]
机构
[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1016/0040-4039(94)02452-H
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of asymmetric dihydroxylation (AD) of the cyclopropylidene derivatives 4a-e followed by enantiospecific 1,2-rearrangement of the resulted diols 5a-e to give the optically active cyclobutanones 7a-e was reported. The synthesis of 7e constitutes an enantioenriched formal total synthesis of (-)-filiformin (8).
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页码:1055 / 1058
页数:4
相关论文
共 20 条
[1]   VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE [J].
GAO, Y ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7538-7539
[2]   CYCLIC SULFATES CONTAINING ACID-SENSITIVE GROUPS AND CHEMOSELECTIVE HYDROLYSIS OF SULFATE ESTERS [J].
KIM, BM ;
SHARPLESS, KB .
TETRAHEDRON LETTERS, 1989, 30 (06) :655-658
[3]   CATALYTIC ASYMMETRIC DIHYDROXYLATION OF TETRASUBSTITUTED OLEFINS [J].
MORIKAWA, K ;
PARK, J ;
ANDERSSON, PG ;
HASHIYAMA, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8463-8464
[4]   THE 1ST ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-LAURENE [J].
NEMOTO, H ;
NAGAMOCHI, M ;
FUKUMOTO, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (22) :1695-1697
[5]  
NEMOTO H, 1993, HETEROCYCLES, V35, P707
[6]   A REMARKABLE SUBSTITUENT EFFECT AN THE ENANTIOSELECTIVITY OF TANDEM ASYMMETRIC EPOXIDATION AND ENANTIOSPECIFIC RING EXPANSION OF CYCLOPROPYLIDENE ALCOHOLS - A NEW ENANTIOCONTROLLED SYNTHESIS OF (-)-DEBROMOAPLYSIN AND (-)-APLYSIN [J].
NEMOTO, H ;
NAGAMOCHI, M ;
ISHIBASHI, H ;
FUKUMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :74-79
[7]   A CONCISE AND ENANTIOSELECTIVE APPROACH TO CYCLOBUTANONES BY TANDEM ASYMMETRIC EPOXIDATION AND ENANTIOSPECIFIC RING EXPANSION OF CYCLOPROPYLIDENE ALCOHOLS - AN ENANTIOCONTROLLED SYNTHESIS OF (+)-ALPHA-CUPARENONE AND (-)-ALPHA-CUPARENONE [J].
NEMOTO, H ;
ISHIBASHI, H ;
NAGAMOCHI, M ;
FUKUMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1707-1712
[8]   A CONCISE ENANTIOCONTROLLED TOTAL SYNTHESIS OF (-)-ALPHA-BISABOLOL AND (+)-4-EPI-ALPHA-BISABOLOL [J].
NEMOTO, H ;
SHIRAKI, M ;
NAGAMOCHI, M ;
FUKUMOTO, K .
TETRAHEDRON LETTERS, 1993, 34 (31) :4939-4942
[9]  
NEMOTO H, 1992, HETEROCYCLES, V33, P549
[10]  
NEMOTO H, IN PRESS HETEROCYCLE