TOTAL SYNTHESIS OF (+/-)-SCOPADULCIC ACID-A - AN ILLUSTRATION OF THE UTILITY OF PALLADIUM-CATALYZED POLYENE CYCLIZATIONS

被引：65

作者：

KUCERA, DJ ^{[1
]}

OCONNOR, SJ ^{[1
]}

OVERMAN, LE ^{[1
]}

机构：

[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 20期

关键词：

D O I：

10.1021/jo00072a006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (+/-)-scopadulcic acid A has been accomplished using an intramolecular bis-Heck cyclization to form the B-D rings of this tetracyclic diterpene with complete stereocontrol.

引用

页码：5304 / 5306

页数：3

共 28 条

[1] CONSTRUCTION OF QUATERNARY CARBON CENTERS BY PALLADIUM-CATALYZED INTRAMOLECULAR ALKENE INSERTIONS - TOTAL SYNTHESIS OF THE AMARYLLIDACEAE ALKALOIDS (+/-)-TAZETTINE AND (+/-)-6A-EPIPRETAZETTINE [J].

ABELMAN, MM ;

OVERMAN, LE ;

TRAN, VD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :6959-6964

[2]

ASANO S, 1990, J BIOL CHEM, V265, P22167

[3]

Chow S.Y., 1974, J FORMOSAN MED ASS, V73, P729

[4] (E)-3-(TRIMETHYLSILYL)-2-PROPEN-1-OL - AN IMPROVED PREPARATION [J].

DENMARK, SE ;

JONES, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4595-4597

[5]

Griffith W. P., 1990, ALDRICHIM ACTA, V23, P13

[6] CYTOTOXIC AND ANTITUMOR-ACTIVITY OF SCOPADULCIC ACID FROM SCOPARIA-DULCIS L [J].

HAYASHI, K ;

HAYASHI, T ;

MORITA, N .

PHYTOTHERAPY RESEARCH, 1992, 6 (01) :6-9

[7] INVITRO AND INVIVO ANTIVIRAL ACTIVITY OF SCOPADULCIC ACID-B FROM SCOPARIA-DULCIS, SCROPHULARIACEAE, AGAINST HERPES-SIMPLEX VIRUS TYPE-1 [J].

HAYASHI, K ;

NIWAYAMA, S ;

HAYASHI, T ;

NAGO, R ;

OCHIAI, H ;

MORITA, N .

ANTIVIRAL RESEARCH, 1988, 9 (06) :345-354

[8]

HAYASHI T, 1990, CHEM PHARM BULL, V38, P239, DOI 10.1248/cpb.38.239

[9] SCOPADULCIC ACID-B, A NEW TETRACYCLIC DITERPENOID FROM SCOPARIA-DULCIS L - ITS STRUCTURE, H+, K+-ADENOSINE TRIPHOSPHATASE INHIBITORY ACTIVITY AND PHARMACOKINETIC BEHAVIOR IN RATS [J].

HAYASHI, T ;

OKAMURA, K ;

KAKEMI, M ;

ASANO, S ;

MIZUTANI, M ;

TAKEGUCHI, N ;

KAWASAKI, M ;

TEZUKA, Y ;

KIKUCHI, T ;

MORITA, N .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (10) :2740-2745

[10] THE CRYSTAL-STRUCTURE OF SCOPADULCIC ACID A FROM PARAGUAYAN CRUDE DRUG TYPYCHA KURATU (SCOPARIA-DULCIS) [J].

HAYASHI, T ;

KISHI, M ;

KAWASAKI, M ;

ARISAWA, M ;

MORITA, N ;

BERGANZA, LH .

JOURNAL OF NATURAL PRODUCTS, 1988, 51 (02) :360-363

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