Radical fragmentation of ω-bromoalkyl cyclobutanones.: A modular approach to eight-membered carbocycles

被引：31

作者：

Oh, HS ^{[1
]}

Lee, HI ^{[1
]}

Cha, JK ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 21期

关键词：

D O I：

10.1021/ol026666a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An eight-membered ring was conveniently appended onto a cycloalkene carboxylate by employing a facile radical cyclization-fragmentation reaction of an omega-bromoalkyl spirocyclobutanone, which was readily accessible by the Kulinkovich cyclopropanation and subsequent electrophilic addition to a 3-bromoalkyl acetal.

引用

收藏

页码：3707 / 3709

页数：3

相关论文

共 35 条

[1] Synthesis of cyclooctenones using intramolecular hydroacylation [J].

Aloise, AD ;

Layton, ME ;

Shair, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (50) :12610-12611

[2]

[Anonymous], 2001, Radicals in Organic Syntheses

[3] The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].

Casiraghi, G ;

Zanardi, F ;

Appendino, G ;

Rassu, G .

CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972

[4] Radical fragmentation of cyclobutanes: An approach to medium ring fused carbocycles [J].

Crimmins, MT ;

Huang, SJ ;

GuiseZawacki, LE .

TETRAHEDRON LETTERS, 1996, 37 (36) :6519-6522

[5] FREE-RADICAL RING EXPANSION OF FUSED CYCLOBUTANONES - STEREOSPECIFIC CONSTRUCTION OF 5,7-CIS-FUSED, 6,7-CIS-FUSED, 7,7-CIS-FUSED, 8,7-CIS-FUSED, AND 5,8-CIS-FUSED BICYCLIC SYSTEMS [J].

DOWD, P ;

ZHANG, W .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7163-7171

[6] FREE RADICAL-MEDIATED RING EXPANSION AND RELATED ANNULATIONS [J].

DOWD, P ;

ZHANG, W .

CHEMICAL REVIEWS, 1993, 93 (06) :2091-2115

[7]

Fossey J., 1995, FREE RADICALS ORGANI

[8]

Giese B., 1986, RADICALS ORGANIC SYN

[9] RADICAL REACTIONS IN NATURAL PRODUCT SYNTHESIS [J].

JASPERSE, CP ;

CURRAN, DP ;

FEVIG, TL .

CHEMICAL REVIEWS, 1991, 91 (06) :1237-1286

[10] DIASTEREOSELECTIVE SYNTHESIS OF TRANS-1,2-DISUBSTITUTED CYCLOPROPANOLS FROM HOMOALLYL OR BIS-HOMOALLYL ESTERS VIA TANDEM INTRAMOLECULAR NUCLEOPHILIC ACYL SUBSTITUTION AND INTRAMOLECULAR CARBONYL ADDITION-REACTIONS MEDIATED BY TI(OPR-I)(4)/2 I-PRMGBR REAGENT [J].

KASATKIN, A ;

SATO, F .

TETRAHEDRON LETTERS, 1995, 36 (34) :6079-6082

← 1 2 3 4 →