Common-intermediate strategy for synthesis of conduritols and inositols via β-hydroxy cyclohexenylsilanes

被引：30

作者：

Heo, JN ^{[1
]}

Holson, EB ^{[1
]}

Roush, WR ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 10期

关键词：

D O I：

10.1021/ol034349d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Syntheses of conduritols B-D and F and (D)-(+)-chiro- and neo-inositols from cyclohexenyl si lane intermediates are described. The key cyclohexylsilane intermediates 5 and 14 were synthesized by stereoselective olefin dihydroxylation of the corresponding cyclohexenylsilanes. Selective Peterson elimination reactions and Fleming-Tamao oxidations of 5 and 14 then delivered the targeted cyclitol derivatives.

引用

收藏

页码：1697 / 1700

页数：4

相关论文

共 48 条

[1] Ruthenium carbene complexes with imidazol-2-ylidene ligands:: Syntheses of conduritol derivatives reveals superior RCM activity [J].

Ackermann, L ;

El Tom, D ;

Fürstner, A .

TETRAHEDRON, 2000, 56 (15) :2195-2202

[2] A DRAMATIC LIGAND EFFECT ON THE RELATIVE REACTIVITIES OF SUBSTITUTED ALKENES WITH OSMIUM-TETROXIDE [J].

ANDERSSON, PG ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7047-7048

[3] Desymmetrization of cyclohexadienylsilanes. Regio-, diastereo-, and enantioselective access to sugar mimics [J].

Angelaud, R ;

Babot, O ;

Charvat, T ;

Landais, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9613-9624

[4] A SIMPLE SYNTHESIS OF CIS-INOSITOL [J].

ANGYAL, SJ ;

ODIER, L ;

TATE, ME .

CARBOHYDRATE RESEARCH, 1995, 266 (01) :143-146

[5] 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

[6] BIOLOGICAL-ACTIVITIES OF CYCLOPHELLITOL [J].

ATSUMI, S ;

IINUMA, H ;

NOSAKA, C ;

UMEZAWA, K .

JOURNAL OF ANTIBIOTICS, 1990, 43 (12) :1579-1585

[7] Synthesis of conduritols and related compounds [J].

Balci, M .

PURE AND APPLIED CHEMISTRY, 1997, 69 (01) :97-104

[8] CONDURITOLS AND RELATED-COMPOUNDS [J].

BALCI, M ;

SUTBEYAZ, Y ;

SECEN, H .

TETRAHEDRON, 1990, 46 (11) :3715-3742

[9] INOSITOL PHOSPHATES AND CELL SIGNALING [J].

BERRIDGE, MJ ;

IRVINE, RF .

NATURE, 1989, 341 (6239) :197-205

[10] INOSITOL TRISPHOSPHATE AND CALCIUM SIGNALING [J].

BERRIDGE, MJ .

NATURE, 1993, 361 (6410) :315-325

← 1 2 3 4 5 →