STEREOCONTROLLED SYNTHESES AND BIOLOGICAL PROFILES OF (+/-)-6,7-DIDEOXYFORSKOLIN AND ITS 13-EPIMER

被引：9

作者：

HASHIMOTO, S ^{[1
]}

BAN, M ^{[1
]}

YANAGIYA, Y ^{[1
]}

SAKATA, S ^{[1
]}

IKEGAMI, S ^{[1
]}

机构：

[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 32期

关键词：

D O I：

10.1016/0040-4039(91)80618-G

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereocontrolled synthesis of the hitherto unknown (+/-)-6,7-dideoxyforskolin has been accomplished, incorporating controlled C-ring annulation with simultaneous creation of the stereogenic center at C-13 via oxymercuration. An alternative attempt at C-ring elaboration via conjugate addition of a higher order vinyl cuprate reagent to dihydropyran-4-one resulted in the exclusive formation of its 13-epimer. These analogues displayed no ability to stimulate adenylate cyclase in rat cerebral cortical membranes.

引用

页码：4027 / 4030

页数：4

共 26 条

[1] THE ANTIHYPERTENSIVE AND POSITIVE INOTROPIC DITERPENE FORSKOLIN - EFFECTS OF STRUCTURAL MODIFICATIONS ON ITS ACTIVITY [J].

BHAT, SV ;

DOHADWALLA, AN ;

BAJWA, BS ;

DADKAR, NK ;

DORNAUER, H ;

DESOUZA, NJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (04) :486-492

[2]

BHAT SV, 1977, TETRAHEDRON LETT, P1669, DOI 10.1016/S0040-4039(01)93245-9

[3] SYNTHESIS OF A CYTOTOXIC VERNOLEPIN PROTOTYPE - OZONIZATION OF SILYLOXYALKENES [J].

CLARK, RD ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1396-1403

[4] SYNTHESIS OF THE ZIEGLER KEY INTERMEDIATE AND RELATED PRECURSORS FOR THE SYNTHESIS OF FORSKOLIN AND ERIGEROL [J].

COLOMBO, MI ;

ZINCZUK, J ;

BACIGALUPPO, JA ;

SOMOZA, C ;

RUVEDA, EA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5631-5639

[5] TOTAL SYNTHESIS OF (+/-)-FORSKOLIN [J].

COREY, EJ ;

JARDINE, PD ;

ROHLOFF, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3672-3673

[6] NEW METHODS FOR CARBOCYCLIC SNYTHESIS APPLICABLE TO GIBBERELLIC ACIDS - STEREOSELECTIVE INTRODUCTION OF ANGULAR VINYL GROUPING AND PINACOLIC CYCLIZATION OF KETO ALDEHYDES [J].

COREY, EJ ;

CARNEY, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (26) :7318-&

[7] RETROSYNTHETIC STUDIES WITH FORSKOLIN [J].

DELPECH, B ;

LETT, R .

TETRAHEDRON LETTERS, 1987, 28 (35) :4061-4064

[8] FORSKOLIN - A LABDANE DITERPENOID WITH ANTIHYPERTENSIVE, POSITIVE INOTROPIC, PLATELET-AGGREGATION INHIBITORY, AND ADENYLATE-CYCLASE ACTIVATING PROPERTIES [J].

DESOUZA, NJ ;

DOHADWALLA, AN ;

REDEN, J .

MEDICINAL RESEARCH REVIEWS, 1983, 3 (02) :201-219

[9] 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

[10] A STEREOCONTROLLED SYNTHESIS OF (+/-)-1,6,7-TRIDEOXYFORSKOLIN [J].

HASHIMOTO, S ;

SONEGAWA, M ;

SAKATA, S ;

IKEGAMI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (01) :24-25

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