A direct entry to carbasugars:: Asymmetric synthesis of 1-epi-(+)-MK7607

被引:32
作者
Grondal, Christoph [1 ]
Enders, Dieter [1 ]
机构
[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
carbasugars; organocatalysis; asymmetric synthesis; aldol reaction; ring-closing metathesis;
D O I
10.1055/s-2006-956495
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short and flexible synthesis of 5a-carbasugars is presented. The combination of a proline-catalyzed aldol reaction and a ring-closing metathesis affords 1-epi-(+)-MK7607 in seven steps with an overall yield of 23%.
引用
收藏
页码:3507 / 3509
页数:3
相关论文
共 51 条
[1]  
[Anonymous], [No title captured]
[2]   PRODUCTION, ISOLATION AND STRUCTURE DETERMINATION OF A NOVEL BETA-GLUCOSIDASE INHIBITOR, CYCLOPHELLITOL, FROM PHELLINUS SP [J].
ATSUMI, S ;
UMEZAWA, K ;
IINUMA, H ;
NAGANAWA, H ;
NAKAMURA, H ;
IITAKA, Y ;
TAKEUCHI, T .
JOURNAL OF ANTIBIOTICS, 1990, 43 (01) :49-53
[3]   BIOLOGICAL-ACTIVITIES OF CYCLOPHELLITOL [J].
ATSUMI, S ;
IINUMA, H ;
NOSAKA, C ;
UMEZAWA, K .
JOURNAL OF ANTIBIOTICS, 1990, 43 (12) :1579-1585
[4]  
BACH G, 1993, LIEBIGS ANN CHEM, P241
[5]   Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].
Berecibar, A ;
Grandjean, C ;
Siriwardena, A .
CHEMICAL REVIEWS, 1999, 99 (03) :779-844
[6]  
BLOCK O, 2000, THESIS U WUPPERTAL G
[7]   An efficient synthesis of valienamine via ring-closing metathesis [J].
Chang, YK ;
Lee, BY ;
Kim, DJ ;
Lee, GS ;
Jeon, HB ;
Kim, KS .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3299-3302
[8]   Formal synthesis of valienamine using ring-closing metathesis [J].
Cumpstey, I .
TETRAHEDRON LETTERS, 2005, 46 (37) :6257-6259
[9]   Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].
Deiters, A ;
Martin, SF .
CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238
[10]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720