ASCENT OF THE ALDOSE SERIES BY 4 CARBON-ATOMS - TOTAL SYNTHESIS OF D-GLYCERO-D-TALO-L-TALO-UNDECOSE PENTAACETONIDE

被引：45

作者：

CASIRAGHI, G ^{[1
]}

COLOMBO, L ^{[1
]}

RASSU, G ^{[1
]}

SPANU, P ^{[1
]}

机构：

[1] CNR,IST APPLICAZIONE TECN CHIM AVANZATE & PROBLEMI AGROBIOL,I-07100 SASSARI,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 06期

关键词：

D O I：

10.1021/jo00006a032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1). The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving C(n+4) butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9. At the end of the eight-step sequence, undecose 9 was prepared in a 5.1% overall yield, which corresponded to a 69.5% average yield per step.

引用

页码：2135 / 2139

页数：5

共 37 条

[1]

ACHMATOWICZ O, 1981, ORGANIC SYNTHESIS TO, P307

[2]

AUGE C, 1990, TETRAHEDRON, V46, P2101

[3] HIGHER-CARBON SUGARS .13. THE CATALYTIC OSMYLATION OF SOME ALPHA,BETA-UNSATURATED OCTURONIC ACID-DERIVATIVES AND A SYNTHESIS OF (MESO)-THREO-GLUCO-OCTITOL [J].

BARNES, JC ;

BRIMACOMBE, JS ;

MCDONALD, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1483-1489

[4] EASY SYNTHESIS OF A C-DISACCHARIDE [J].

BOSCHETTI, A ;

NICOTRA, F ;

PANZA, L ;

RUSSO, G ;

ZUCCHELLI, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (16) :1085-1086

[5] SYNTHESIS OF ENANTIOMERICALLY PURE 2,3-DIDEOXY-HEPT-2-ENONO-1,4-LACTONE DERIVATIVES VIA DIASTEREOSELECTIVE ADDITION OF 2-(TRIMETHYLSILOXY)FURAN TO D-GLYCERALDEHYDE AND D-SERINAL-BASED 3-CARBON SYNTHONS [J].

CASIRAGHI, G ;

COLOMBO, L ;

RASSU, G ;

SPANU, P .

TETRAHEDRON LETTERS, 1989, 30 (39) :5325-5328

[6] THE 4-CARBON ELONGATION OF ALDEHYDO SUGARS USING 2-(TRIMETHYLSILOXY)-FURAN - A BUTENOLIDE ROUTE TO HIGHER MONOSACCHARIDES [J].

CASIRAGHI, G ;

COLOMBO, L ;

RASSU, G ;

SPANU, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2565-2567

[7] THE 4-CARBON ELONGATION OF 3-CARBON CHIRAL SYNTHONS USING 2-(TRIMETHYLSILOXY)FURAN - HIGHLY STEREOCONTROLLED ENTRY TO ENANTIOMERICALLY PURE 7-CARBON ALPHA,BETA-UNSATURATED 2,3-DIDEOXY-ALDONOLACTONES [J].

CASIRAGHI, G ;

COLOMBO, L ;

RASSU, G ;

SPANU, P ;

FAVA, GG ;

BELICCHI, MF .

TETRAHEDRON, 1990, 46 (16) :5807-5824

[8] TOTAL SYNTHESIS OF OCTOSYL ACID-A - INTRAMOLECULAR WILLIAMSON REACTION VIA A CYCLIC STANNYLENE DERIVATIVE [J].

DANISHEFSKY, SJ ;

HUNGATE, R ;

SCHULTE, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7434-7440

[9] A STEREOSELECTIVE TOTALLY SYNTHETIC ROUTE TO METHYL ALPHA-PERACETYLHIKOSAMINIDE [J].

DANISHEFSKY, SJ ;

MARING, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (06) :2193-2204

[10] STEREOSELECTIVE TOTAL SYNTHESES OF THE NATURALLY-OCCURRING ENANTIOMERS OF N-ACETYLNEURAMINIC ACID AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID - A NEW AND STEREOSPECIFIC APPROACH TO SIALO AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID CONJUGATES [J].

DANISHEFSKY, SJ ;

DENINNO, MP ;

CHEN, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (12) :3929-3940

← 1 2 3 4 →