THE STEREOSELECTIVE SYNTHESIS OF UNSATURATED 9-MEMBERED LACTONES USING THE MALHERBE-BELLUS VARIANT OF THE CLAISEN REARRANGEMENT

被引：17

作者：

KLING, MR ^{[1
]}

MCNAUGHTONSMITH, GA ^{[1
]}

TAYLOR, RJK ^{[1
]}

机构：

[1] UNIV E ANGLIA,SCH CHEM SCI,NORWICH NR4 7TJ,NORFOLK,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 21期

关键词：

D O I：

10.1039/c39930001593

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting DELTA5-dichlorolactones are exclusively trans but dechlorination using Bu3SnH-AIBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.

引用

页码：1593 / 1595

页数：3

共 26 条

[1] SYNTHESIS OF MACROCYCLIC LACTONES - APPROACHES TO COMPLEX MACROLIDE ANTIBIOTICS [J].

BACK, TG .

TETRAHEDRON, 1977, 33 (23) :3041-3059

[2]

BORER BC, 1992, SYNLETT, P117

[3]

BORER BC, 1990, J CHEM RES-S, P162

[4]

BRADLEY HM, 1992, SYNLETT, P479

[5]

BURFORD SC, 1986, J CHEM SOC P1, P1809

[6]

COPE AC, 1959, J AM CHEM SOC, V81, P3153

[7] STUDIES TOWARDS THE SYNTHESIS OF OBTUSENYNE - A CLAISEN REARRANGEMENT APPROACH TO UNSATURATED 9-MEMBERED LACTONES [J].

CURTIS, NR ;

HOLMES, AB ;

LOONEY, MG .

TETRAHEDRON, 1991, 47 (34) :7171-7178

[8] STUDIES TOWARDS THE SYNTHESIS OF OBTUSENYNE - SYNTHESIS OF THE HEXAHYDROOXONIN NUCLEUS [J].

CURTIS, NR ;

HOLMES, AB ;

LOONEY, MG .

TETRAHEDRON LETTERS, 1992, 33 (05) :671-674

[9] THE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF THE NOVEL ICHTHYOTOXIC DIACYLGLYCEROLS, UMBRACULUMIN-A AND UMBRACULUMIN-C [J].

DEMEDEIROS, EF ;

HERBERT, JM ;

TAYLOR, RJK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2725-2730

[10] AN EFFICIENT SYNTHESIS OF THE ANTISECRETORY PROSTAGLANDIN ENISOPROST [J].

DYGOS, JH ;

ADAMEK, JP ;

BABIAK, KA ;

BEHLING, JR ;

MEDICH, JR ;

NG, JS ;

WIECZOREK, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2549-2552

← 1 2 3 →