SYNTHESIS AND STEREOCHEMISTRY OF DESACETOXYMATRICARIN AND STEREOCHEMISTRY OF MATRICARIN

被引:50
作者
WHITE, EH
EGUCHI, S
MARX, JN
机构
[1] Department of Chemistry, The Johns Hopkins University, Baltimore
关键词
D O I
10.1016/S0040-4020(01)82761-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Desacetoxymatricarin (IV), a sesquiterpene lactone found in the genus Artemisia and in the form of 8-hydroxy and acetoxy derivatives in the genus Achillea, has been synthesized from α-santonin by a sequence that allows assignment of the full stereochemistry. The stereochemistry of matricarin (V) has also been determined. The unusual stability to dehydration of some of the cyclopentyl-type alcohols, which were intermediates in the synthesis, is discussed. © 1969.
引用
收藏
页码:2099 / +
页数:1
相关论文
共 56 条
[41]  
PINHEY JT, 1963, TETRAHEDRON LETT, P275
[42]  
RICHARDS JH, 1964, BIOSYNTHESIS STEROID, P231
[43]  
RYBALKO KS, 1963, ZH OBSHCH KHIM+, V33, P2734
[44]  
RYBALKO KS, 1961, MED PROM SSSR, V15, P25
[45]   UBER DAS KETO-ENOL-GLEICHGEWICHT BEI CYCLISCHEN ALPHA-DIKETONEN [J].
SCHWARZENBACH, G ;
WITTWER, C .
HELVETICA CHIMICA ACTA, 1947, 30 (02) :663-669
[46]  
SMOLENSKI SJ, 1967, LLOYD, V30, P144
[47]  
SUCHY M, 1964, COLLECT CZECH CHEM C, V29, P1829
[48]   STUDIES ON SESQUITERPENOIDS .6. SYNTHESIS OF 3,5,8-TRIMETHYLAZULENO(6,5-N)FURAN )L)INDERAZULENE ) [J].
TAKEDA, K ;
MINATO, H ;
ISHIKAWA, M .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (AUG) :2591-&
[49]   MECHANISMS OF OXIDATION BY COMPOUNDS OF CHROMIUM AND MANGANESE [J].
WATERS, WA .
QUARTERLY REVIEWS, 1958, 12 (04) :277-300
[50]  
WHITE EH, 1963, TETRAHEDRON LETT, P137