Synthesis of a 2,7-dioxatricyclo[4.2.1.0(3,8)]nonane: A model study for possible application in a synthesis of dictyoxetane

被引：42

作者：

Marshall, KA ^{[1
]}

Mapp, AK ^{[1
]}

Heathcock, CH ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 26期

关键词：

D O I：

10.1021/jo961680k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the synthesis of the 2,7-dioxatricyclo[4.2.1.0(3,8)]nonane ring system characteristic of the marine diterpene dictyoxetane has been developed. This method utilizes a dipolar cycloaddition of a 3-oxidopyrylium salt to create the carbon skeleton (Scheme 1) and employs an intramolecular S(N)2 displacement to form the oxetane ring (Schemes 9, 10, 13). The route described could easily be adapted to incorporate additional functionality, making it potentially useful in a total synthesis of dictyoxetane.

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页码：9135 / 9145

页数：11

相关论文

共 49 条

[1] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES [J].

ACHMATOWICZ, O ;

BUKOWSKI, P ;

SZECHNER, B ;

ZWIERZCHOWSKA, Z ;

ZAMOJSKI, A .

TETRAHEDRON, 1971, 27 (10) :1973-+

[2]

ANTONIOLETTI R, 1993, TETRAHEDRON LETT, V44, P7089

[3] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].

BAX, A ;

SUMMERS, MF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094

[4] SENSITIVITY-ENHANCED TWO-DIMENSIONAL HETERONUCLEAR SHIFT CORRELATION NMR-SPECTROSCOPY [J].

BAX, A ;

SUBRAMANIAN, S .

JOURNAL OF MAGNETIC RESONANCE, 1986, 67 (03) :565-569

[5] SELECTION OF COHERENCE-TRANSFER PATHWAYS IN NMR PULSE EXPERIMENTS [J].

BODENHAUSEN, G ;

KOGLER, H ;

ERNST, RR .

JOURNAL OF MAGNETIC RESONANCE, 1984, 58 (03) :370-388

[6] ARE NUCLEOPHILIC BIMOLECULAR CONCERTED REACTIONS INVOLVING 4 OR MORE BONDS A MYTH [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1970, 3 (09) :281-&

[7] DIRECTED HOMOGENEOUS HYDROGENATION [J].

BROWN, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (03) :190-203

[8] THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS [J].

BURGESS, EM ;

PENTON, HR ;

TAYLOR, EA .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :26-31

[9] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[10] TOTAL SYNTHESIS OF RAC-9,11-DEHYDRODIGITOXIGENIN 3-TETRAHYDROPYRANYL ETHER [J].

DANIEWSKI, AR ;

KABAT, MM ;

MASNYK, M ;

WICHA, J ;

WOJCIECHOWSKA, W ;

DUDDECK, H .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (20) :4855-4858

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