STUDIES IN MARINE MACROLIDE SYNTHESIS - BORON AND SILICON-MEDIATED COUPLING STRATEGIES FOR SWINHOLIDE-A

被引：48

作者：

PATERSON, I

CUMMING, JG

SMITH, JD

WARD, RA

机构：

[1] University Chemical Laboratory, Cambridge, CB2 1EW, Lensfield Road

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 03期

关键词：

D O I：

10.1016/0040-4039(94)85075-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of aldehyde 6 with enol borinates 7 gives adduct 10 preferentially, whereas the allylsilane 18 provides the epimeric adduct 11 with 95% ds. Aldehyde 2 reacts mainly by si-face attack with simple Z enol borinates, which can be overturned by reagent control from (+)-25.

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页码：441 / 444

页数：4

相关论文

共 20 条

[1] TRANSITION-STATE MODELING OF THE ALDOL REACTION OF BORON ENOLATES - A FORCE-FIELD APPROACH [J].

BERNARDI, A ;

CAPELLI, AM ;

GENNARI, C ;

GOODMAN, JM ;

PATERSON, I .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3576-3581

[2] ENOLBORATION .1. DICYCLOHEXYLCHLOROBORANE TRIETHYLAMINE AS A CONVENIENT REAGENT FOR ENOLBORATION OF KETONES AND OTHER CARBONYL DERIVATIVES [J].

BROWN, HC ;

DHAR, RK ;

GANESAN, K ;

SINGARAM, B .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :499-504

[3] STRUCTURE OF SWINHOLIDE-A, A NEW MACROLIDE FROM THE MARINE SPONGE THEONELLA-SWINHOEI [J].

CARMELY, S ;

KASHMAN, Y .

TETRAHEDRON LETTERS, 1985, 26 (04) :511-514

[4]

DOI M, 1991, J ORG CHEM, V56, P3629, DOI 10.1021/jo00011a033

[5] REVERSAL OF ALDEHYDE DIASTEREOFACIAL SELECTIVITY IN A METHYL KETONE ALDOL REACTION - APPLICATION TO THE SYNTHESIS OF THE CALYCULIN SPIROKETAL [J].

EVANS, DA ;

GAGE, JR .

TETRAHEDRON LETTERS, 1990, 31 (43) :6129-6132

[6] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

NELSON, JV ;

VOGEL, E ;

TABER, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111

[7] ENOLIZATION OF KETONES BY DIALKYLBORON CHLORIDES AND TRIFLATES - A MODEL FOR THE EFFECT OF REAGENT LEAVING GROUP, SUBSTRATE STRUCTURE AND AMINE BASE [J].

GOODMAN, JM ;

PATERSON, I .

TETRAHEDRON LETTERS, 1992, 33 (47) :7223-7226

[8] ABSOLUTE STEREOSTRUCTURE OF SWINHOLIDE-A, A POTENT CYTOTOXIC MACROLIDE FROM THE OKINAWAN MARINE SPONGE THEONELLA-SWINHOEI [J].

KITAGAWA, I ;

KOBAYASHI, M ;

KATORI, T ;

YAMASHITA, M ;

TANAKA, J ;

DOI, M ;

ISHIDA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3710-3712

[9] MARINE NATURAL-PRODUCTS .23. 3 NEW CYTOTOXIC DIMERIC MACROLIDES, SWINHOLIDE-B AND SWINHOLIDE-C AND ISOSWINHOLIDE-A, CONGENERS OF SWINHOLIDE-A, FROM THE OKINAWAN MARINE SPONGE THEONELLA-SWINHOEI [J].

KOBAYASHI, M ;

TANAKA, J ;

KATORI, T ;

KITAGAWA, I .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) :2960-2966

[10]

KOBAYASHI M, 1990, CHEM PHARM BULL, V38, P2409