ENANTIOSPECIFIC SYNTHESIS OF THE TRICYCLIC NUCLEUS OF ACETOXYCRENULIDE BY CLAISEN RING EXPANSION

被引：24

作者：

EZQUERRA, J ^{[1
]}

WEI, H ^{[1
]}

PAQUETTE, LA ^{[1
]}

机构：

[1] OHIO STATE UNIV,EVANS CHEM LABS,COLUMBUS,OH 43210

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(00)97221-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The known R lactone 4 has been transformed in 9 steps into optically pure 2, a molecule possessing the ring system characteristic of the crenulide diterpenes. In the key step, chirality transfer is accomplished via a Z-selective Claisen ring expansion. © 1990.

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页码：6979 / 6982

页数：4

相关论文

共 30 条

[1] PREPARATION AND DIELS-ALDER REACTIONS OF 5-ALKENYL 2-(3H)-FURANONES [J].

ALEXANDRE, C ;

ROUESSAC, F ;

TABTI, B .

TETRAHEDRON LETTERS, 1985, 26 (44) :5453-5456

[2] SYNTHESIS APPLICATION OF CYCLIZATION OF TERTIARY ALPHA ETHYLENIC ALCOHOLS TO ALPHA BROMOTETRAHYDROFURANS UNDER ACTION OF N-BROMOSUCCINIMIDE .2. CYCLIZATION OF (+) NEROLIDOL TO 2,5-DIMETHYL-2-(4-METHYLPENT-3-ENYL)CYCLOHEPT-4-ENONE, 3,3,7,10-TETRAMETHYL-2-OXATRICYCLO [5,5.0.0.1,4]DODEC-9-ENE, BETA ACORATRIENE, 2,8-CEDRADIENE, EPI-2-ALPHA CEDRENE AND ALPHA CEDRENE [J].

DEMOLE, E ;

ENGGIST, P ;

BORER, C .

HELVETICA CHIMICA ACTA, 1971, 54 (07) :1845-&

[3]

FENICAL W, 1978, MARINE NATURAL PRODU, V2, P173

[4] THE STEREOSELECTIVE ALPHA-ALKYLATION OF CHIRAL BETA-HYDROXY ESTERS AND SOME APPLICATIONS THEREOF [J].

FRATER, G ;

MULLER, U ;

GUNTHER, W .

TETRAHEDRON, 1984, 40 (08) :1269-1277

[5] N-PHENYLSELENOPHTHALIMIDE - A USEFUL REAGENT FOR THE FACILE TRANSFORMATION OF (1) CARBOXYLIC-ACIDS INTO EITHER SELENOL ESTERS OR AMIDES AND (2) ALCOHOLS INTO ALKYL PHENYL SELENIDES [J].

GRIECO, PA ;

JAW, JY ;

CLAREMON, DA ;

NICOLAOU, KC .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1215-1217

[6] STRUCTURE AND CONFORMATION OF PACHYLACTONE, A NEW DITERPENE ISOLATED FROM THE BROWN ALGA, PACHYDICTYON-CORIACEUM [J].

ISHITSUKA, M ;

KUSUMI, T ;

KAKISAWA, H ;

KAWAKAMI, Y ;

NAGAI, Y ;

SATO, T .

TETRAHEDRON LETTERS, 1983, 24 (46) :5117-5120

[7] CLAISEN-BASED STRATEGY FOR THE DENOVO CONSTRUCTION OF BASMANE DITERPENES - ENANTIOSPECIFIC SYNTHESIS OF (+)-7,8-EPOXY-2-BASMEN-6-ONE [J].

KANG, HJ ;

PAQUETTE, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3252-3253

[8] ASYMMETRIC ALDOL REACTION OF AMIDE ENOLATES BEARING TRANS-2,5-DISUBSTITUTED PYRROLIDINES AS CHIRAL AUXILIARIES [J].

KATSUKI, T ;

YAMAGUCHI, M .

TETRAHEDRON LETTERS, 1985, 26 (47) :5807-5810

[9] GENERAL-APPROACH TO ANNULATED 4-CYCLOOCTENONES BY ALIPHATIC CLAISEN REARRANGEMENT - STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-PRECAPNELLADIENE [J].

KINNEY, WA ;

COGHLAN, MJ ;

PAQUETTE, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (25) :7352-7360

[10] CLAISEN REARRANGEMENT OF 6-ALKENYL-2-METHYLENETETRAHYDROPYRANS - A NEW APPROACH TO ANNULATED 4-CYCLOOCTENONES AND A STEREOSPECIFIC SYNTHESIS OF PRECAPNELLADIENE [J].

KINNEY, WA ;

COGHLAN, MJ ;

PAQUETTE, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (22) :6868-6870