CYCLIZATION OF A CHIRAL ALPHA-(DELTA'-BENZYLOXYALKYL)ACRYLATE TO A NOVEL TETRAHYDROFURAN DERIVATIVE

被引：12

作者：

DREWES, SE

NJAMELA, OL

ROOS, GHP

机构：

[1] Department of Chemistry, University of Natal, Pietermaritzburg, 3200

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 12期

关键词：

TETRAHYDROFURANS; ACRYLATES; ALPHA-(DELTA'-HYDROXYALKYL); ALDEHYDES; BETA-HYDROXYALKYL;

D O I：

10.1002/cber.19901231231

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methyl 3-hydroxy-2-(iodomethyl)-5-methyltetrahydrofuran-2-carboxylate (4) is synthesized from (3S)-3-(benzyloxy)butanal (2) via methyl 5-(benzyloxy)-3-hydroxy-2-methylenehexanoate (3a) as intermediate.

引用

页码：2455 / 2456

页数：2

共 13 条

[1] DIASTEREOSELECTIVITY IN THE SYNTHESIS OF 3(2H)-FURANONES - TOTAL SYNTHESIS OF (+)-MUSCARINE [J].

ADAMS, J ;

POUPART, MA ;

GRENIER, L .

TETRAHEDRON LETTERS, 1989, 30 (14) :1753-1756

[2] HIGH DIASTEREOFACE SELECTION IN AN ESTER ENOLATE ADDITION TO ALPHA-ALKOXY ALDEHYDES - STEREOSELECTIVE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS [J].

BANFI, L ;

BERNARDI, A ;

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) :3784-3790

[3]

CHIKASHITA H, 1989, SYNTHETIC COMMUN, V30, P3811

[4] SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].

DREWES, SE ;

ROOS, GHP .

TETRAHEDRON, 1988, 44 (15) :4653-4670

[5] FACILE DIASTEREOSELECTIVE SYNTHESIS OF 2,6-DIALKYL-5-METHYLENE-1,3-DIOXAN-4-ONES VIA ALPHA-ACTIVATED VINYL ESTERS [J].

DREWES, SE ;

EMSLIE, ND ;

KARODIA, N ;

KHAN, AA .

CHEMISCHE BERICHTE, 1990, 123 (06) :1447-1448

[6] REAGENT-CONTROLLED ADDITION OF (R)-2-HYDROXY-1,2,2-TRIPHENYLETHYL AND (S)-2-HYDROXY-1,2,2-TRIPHENYLETHYL ACETATE TO CHIRAL ALDEHYDES [J].

MAHLER, U ;

DEVANT, RM ;

BRAUN, M .

CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (11) :2035-2044

[7] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].

MANCUSO, AJ ;

HUANG, SL ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482

[8] THE REDUCTION OF ACID AMIDES WITH LITHIUM ALUMINUM HYDRIDE [J].

MICOVIC, VM ;

MIHAILOVIC, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (09) :1190-1200

[9] A NEW METHOD FOR STEREOCHEMICAL CONTROL OF MICROBIAL REDUCTION - REDUCTION OF BETA-KETO-ESTERS WITH BAKERS-YEAST IMMOBILIZED BY MAGNESIUM ALGINATE [J].

NAKAMURA, K ;

KAWAI, Y ;

OKA, S ;

OHNO, A .

TETRAHEDRON LETTERS, 1989, 30 (17) :2245-2246

[10] STEREOCHEMICAL CONTROL IN MICROBIAL REDUCTION .5. EFFECT OF ALLYL ALCOHOL ON REDUCTION OF BETA-KETO-ESTERS BY BAKERS-YEAST [J].

NAKAMURA, K ;

INOUE, K ;

USHIO, K ;

OKA, S ;

OHNO, A .

CHEMISTRY LETTERS, 1987, (04) :679-682

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