De novo enantioselective syntheses of galacto-sugars and deoxy sugars via the iterative dihydroxylation of dienoate

被引：70

作者：

Ahmed, MM ^{[1
]}

Berry, BP ^{[1
]}

Hunter, TJ ^{[1
]}

Tomcik, DJ ^{[1
]}

O'Doherty, GA ^{[1
]}

机构：

[1] W Virginia Univ, Dept Chem, Morgantown, WV 26506 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 04期

关键词：

D O I：

10.1021/ol050044i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient route to various sugar lactones has been developed. Key to the overall transformation is the sequential osmium-catalyzed dihydroxylation of 2,4-dienoates. The simplest (one-step/racemic) example of this reaction occurs when the dihydroxylation is performed with aqueous NMO in MeOH. When the first dihydroxylation is performed using the AD-mix procedure, an enantioselective variant results. When a matched AD-mix procedure is used for the second dihydroxylation, an exceedingly diastereo- and enantioselective synthesis of galacto-1,4-lactone results.

引用

页码：745 / 748

页数：4

共 25 条

[1] De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction
Babu, RS
Zhou, M
O'Doherty, GA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) : 3428 - 3429
[2] A palladium-catalyzed glycosylation reaction: The de novo synthesis of natural and unnatural glycosides
Babu, RS
O'Doherty, GA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) : 12406 - 12407
[3] Thermal/hyperbaric heterocycloaddition of 1,4-dialkoxy-1,3-dienes:: The de novo (E,Z) way to sugars
Bataille, C
Bégin, G
Guillam, A
Lemiègre, L
Lys, C
Maddaluno, J
Toupet, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (23) : 8054 - 8062
[4] SELECTIVE ASYMMETRIC DIHYDROXYLATION OF POLYENES
BECKER, H
SOLER, MA
SHARPLESS, KB
[J]. TETRAHEDRON, 1995, 51 (05) : 1345 - 1376
[5] Chemical synthesis of GDP-L-galactose and analogues
Binch, H
Stangier, K
Thiem, J
[J]. CARBOHYDRATE RESEARCH, 1998, 306 (03) : 409 - 419
[6] The asymmetric synthesis of D-galactose via an iterative syn-glycolate aldol strategy
Davies, SG
Nicholson, RL
Smith, AD
[J]. SYNLETT, 2002, (10) : 1637 - 1640
[7] Ernst B., 2000, CARBOHYD CHEM-SPR
[8] Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics
Gijsen, HJM
Qiao, L
Fitz, W
Wong, CH
[J]. CHEMICAL REVIEWS, 1996, 96 (01) : 443 - 473
[9] Syntheses of four D- and L-hexoses via diastereoselective and enantioselective dihydroxylation reactions
Harris, JM
Keränen, MD
Nguyen, H
Young, VG
O'Doherty, GA
[J]. CARBOHYDRATE RESEARCH, 2000, 328 (01) : 17 - 36
[10] Modern methods of monosaccharide synthesis from non-carbohydrate sources
Hudlicky, T
Entwistle, DA
Pitzer, KK
Thorpe, AJ
[J]. CHEMICAL REVIEWS, 1996, 96 (03) : 1195 - 1220

← 1 2 3 →