Furanose synthesis via regioselective dihydroxylation of 1-silyloxy-1,3-dienes:: Application to the furanose unit of 4-epi-hygromycin A

被引：5

作者：

Armstrong, A

Gethin, DM

Wheelhouse, CJ

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] Pfizer Anim Hlth, Vet Med Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

SYNLETT | 2004年 / 02期

关键词：

alkenes; dihydroxylation; osmium; regioselective; oxidations;

D O I：

10.1055/s-2003-44979

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric dihydroxylation of a 1-silyloxy-1,3-diene is shown to occur regioselectively on the non-oxygenated alkene. Second dihydroxylation is complicated by over-oxidation to the dione and epimerisation of reaction products. However, subsequent manipulations including selective oxidation of a primary alcohol allow synthesis of a protected furanose corresponding to that present in C4-epi-hygromycin.

引用

收藏

页码：350 / 352

页数：3

相关论文

共 21 条

[1] Total synthesis of (+)-zaragozic acid C [J].

Armstrong, A ;

Barsanti, PA ;

Jones, LH ;

Ahmed, G .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :7020-7032

[2] Mono-osmylation of dehydroamino acid dienes: Synthesis of dehydroamino acids related to the azinomycins [J].

Armstrong, RW ;

Tellew, JE ;

Moran, EJ .

TETRAHEDRON LETTERS, 1996, 37 (04) :447-450

[3] SELECTIVE ASYMMETRIC DIHYDROXYLATION OF POLYENES [J].

BECKER, H ;

SOLER, MA ;

SHARPLESS, KB .

TETRAHEDRON, 1995, 51 (05) :1345-1376

[4] A STEREOSELECTIVE ROUTE TO THE SUGAR-CINNAMATE UNIT OF HYGROMYCIN-A [J].

BUCHANAN, JG ;

HILL, DG ;

WIGHTMAN, RH ;

BODDY, IK ;

HEWITT, BD .

TETRAHEDRON, 1995, 51 (21) :6033-6050

[5] TOTAL SYNTHESIS OF ANTIBIOTIC HYGROMYCIN-A [J].

CHIDA, N ;

OHTSUKA, M ;

NAKAZAWA, K ;

OGAWA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2976-2983

[6] Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose [J].

Cox, LR ;

DeBoos, GA ;

Fullbrook, JJ ;

Percy, JM ;

Spencer, NS ;

Tolley, M .

ORGANIC LETTERS, 2003, 5 (03) :337-339

[7] Trichloroisocyanuric/TEMPO oxidation of alcohols under mild conditions: A close investigation [J].

De Luca, L ;

Giacomelli, G ;

Masala, S ;

Porcheddu, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4999-5001

[8] A very mild and chemoselective oxidation of alcohols to carbonyl compounds [J].

De Luca, L ;

Giacomelli, G ;

Porcheddu, A .

ORGANIC LETTERS, 2001, 3 (19) :3041-3043

[9]

deNooy AEJ, 1996, SYNTHESIS-STUTTGART, P1153

[10] Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts [J].

Einhorn, J ;

Einhorn, C ;

Ratajczak, F ;

Pierre, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7452-7454