SYNTHETIC STUDIES TOWARD PAEONIFLORIN - PREPARATION OF THE HIGHLY FUNCTIONALIZED PINANE SKELETON UTILIZING INTRAMOLECULAR HOSOMI-SAKURAI REACTION

被引：0

作者：

HATAKEYAMA, S ^{[1
]}

KAWAMURA, M ^{[1
]}

SHIMANUKI, E ^{[1
]}

SAIJO, K ^{[1
]}

TAKANO, S ^{[1
]}

机构：

[1] TOHOKU UNIV, INST PHARMACEUT SCI, SENDAI, MIYAGI 980, JAPAN

来源：

SYNLETT | 1992年 / 02期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to the highly functionalized pinane unit present in paeniflorin (1) is described. The sequence employs the newly developed reagent, [4-(1,3-dithian-2-yl)-2-butenyl]trimethylsilane (6), which serves as an annulating agent by a combination of Michael addition and intramolecular Hosomi-Sakurai reaction.

引用

页码：114 / 116

页数：3

共 20 条

[1] CHEMICAL STUDIES ON ORIENTAL PLANT DRUGS .23. PAEONIFLORIN A GLUCOSIDE OF CHINESE PAEONY ROOT [J].

AIMI, N ;

INABA, M ;

WATANABE, M ;

SHIBATA, S .

TETRAHEDRON, 1969, 25 (09) :1825-&

[2]

AIMI N, 1985, J TRADITIONAL SINOJA, V6, P51

[3] NATURAL ABUNDANCE C-13-C-13 COUPLING OBSERVED VIA DOUBLE-QUANTUM COHERENCE [J].

BAX, A ;

FREEMAN, R ;

KEMPSELL, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (14) :4849-4851

[4] INDUCED CONJUGATE ADDITION OF SIMPLE 2-LITHIO-1,3-DITHIANS TO CYCLIC-ALPHA,BETA-UNSATURATED KETONES [J].

BROWN, CA ;

YAMAICHI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (03) :100-101

[5]

FLEMING I, 1979, SYNTHESIS-STUTTGART, P446

[6]

FUJIWARA M, 1990, JPN J NEUROPSYCHOPH, V12, P217

[7] ORGANOSELENIUM CHEMISTRY - FACILE ONE-STEP SYNTHESIS OF ALKYL ARYL SELENIDES FROM ALCOHOLS [J].

GRIECO, PA ;

GILMAN, S ;

NISHIZAWA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1485-1486

[8]

HARADA M, 1985, J TRAD SINO JAPANESE, V6, P45

[9]

HIKINO H, 1985, EC MED PLANT RES, P55

[10] CHEMICAL STUDIES ON ORIENTAL PLANT DRUGS .33. ABSOLUTE STRUCTURES OF PAEONIFLORIN, ALBIFLORIN, OXYPAEONIFLORIN AND BENZOYLPAEONIFLORIN ISOLATED FROM CHINESE PEONY ROOT [J].

KANEDA, M ;

SHIBATA, S ;

IITAKA, Y .

TETRAHEDRON, 1972, 28 (16) :4309-+

← 1 2 →