A NEW SYNTHESIS OF SUBSTITUTED BUTENOLIDES VIA CATION-INITIATED RING EXPANSION ELIMINATION OF BETA-LACTONES

被引：16

作者：

BLACK, TH

HUANG, JH

机构：

[1] Department of Chemistry, Eastern Illinois University Charleston

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)60304-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

When treated with silver ion, gamma-bromo beta-lactones, available via bromolactonization, undergo a ring expansion/elimination reaction to afford substituted butenolides.

引用

页码：1411 / 1412

页数：2

共 12 条

[1] A NEW SYNTHESIS OF 3-CHLORO BUTENOLIDES VIA REARRANGEMENT OF 3,3-DICHLORO BETA LACTONES [J].

BLACK, TH ;

MCDERMOTT, TS .

SYNTHETIC COMMUNICATIONS, 1990, 20 (19) :2959-2964

[2] A FACILE 3-ALKYL BUTENOLIDE ANNULATION SEQUENCE [J].

BLACK, TH ;

MCDERMOTT, TS ;

BROWN, GA .

TETRAHEDRON LETTERS, 1991, 32 (45) :6501-6502

[3] A UNIQUE 3-CHLOROBUTENOLIDE ANNULATION SEQUENCE [J].

BLACK, TH ;

MCDERMOTT, TS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (03) :184-185

[4] STUDIES DIRECTED TOWARD THE SYNTHESIS OF THE EREMANTHOLIDES .1. PREPARATION OF A RING A/B MODEL SYSTEM VIA A CONJUGATE ADDITION-ACYLATION PROTOCOL [J].

BOECKMAN, RK ;

HECKENDORN, DK ;

CHINN, RL .

TETRAHEDRON LETTERS, 1987, 28 (31) :3551-3554

[5] SYNTHESIS OF ENANTIOMERICALLY PURE GAMMA-(MENTHYLOXY)BUTENOLIDES AND (R)-2-METHYL-1,4-BUTANEDIOL AND (S)-2-METHYL-1,4-BUTANEDIOL [J].

FERINGA, BL ;

DELANGE, B ;

DEJONG, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2471-2475

[6] STEREOCHEMICAL CONTROL OF NATURES BIOSYNTHETIC PATHWAYS - A GENERAL STRATEGY FOR THE SYNTHESIS OF POLYPROPIONATE-DERIVED STRUCTURAL UNITS FROM A SINGLE CHIRAL PROGENITOR [J].

HANESSIAN, S ;

MURRAY, PJ .

TETRAHEDRON, 1987, 43 (21) :5055-5072

[7] RHODIUM CARBONYL-CATALYZED CARBONYLATION OF UNSATURATED-COMPOUNDS .5. CROSS-HYDROCARBONYLATION OF 1-ALKYNE AND ETHYLENE BY RHODIUM CARBONYL CATALYST MODIFIED WITH PHOSPHINES [J].

HONG, PB ;

MISE, T ;

YAMAZAKI, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 412 (1-2) :291-300

[8] SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-TRIMETHYLSILYL DELTA(ALPHA,BETA)BUTENOLIDES AND THEIR CONVERSION INTO VARIOUS BUTENOLIDES AND SATURATED GAMMA-LACTONES [J].

ITO, T ;

OKAMOTO, S ;

SATO, F .

TETRAHEDRON LETTERS, 1990, 31 (44) :6399-6402

[9] NEW GENERAL ASYMMETRIC-SYNTHESIS OF VERSATILE GAMMA-ALKYLATED BUTENOLIDES AND ITS APPLICATION TO EXPEDITIOUS SYNTHESIS OF THE CHIRAL GEISSMAN-WAISS LACTONES USEFUL FOR (+)-RETRONECINE SYNTHESIS [J].

NAGAO, Y ;

DAI, WM ;

OCHIAI, M ;

SHIRO, M .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5211-5217

[10]

NEWAZ SS, 1977, ALDRICHIM ACTA, V10, P64

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