Stereocontrolled synthesis of spirocyclopropane sugars and their application to asymmetric formation of tertiary chiral centres: A route to 2,2'-dialkylated pyranose subunit (C-18-C-23) of lasonolide A

被引：26

作者：

Gurjar, MK

Kumar, P

Rao, BV

机构：

[1] Indian Inst. of Chemical Technology

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 47期

关键词：

D O I：

10.1016/0040-4039(96)01991-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route to asymmetric formation of tertiary chiral centres of sugars via 2,2'-spirocyclopropane derivatives has been described. This route forms the basis of our proposed synthesis of the C-18-C-23 subunit of lasonolide A. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

收藏

页码：8617 / 8620

页数：4

相关论文

共 12 条

[1]

ENDERS D, 1994, PROTECTING GROUPS, P46

[2] CHEMISTRY OF 2-CARBENABICYCLO[3.2.1]OCTADIENE [J].

FREEMAN, PK ;

SWENSON, KE .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2033-2039

[3] ZINC DUST-CUPROUS CHLORIDE PROMOTED CYCLOPROPANATIONS OF ALLYLIC ALCOHOLS USING ETHYLIDENE IODIDE [J].

FRIEDRICH, EC ;

BIRESAW, G .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (09) :1615-1618

[4]

FURUKAWA J, 1968, TETRAHEDRON LETT, P3495

[5] SYNTHESIS OF CYCLOPROPANES BY REACTION OF OLEFINS WITH DIALKYLZINC AND METHYLENE IODIDE [J].

FURUKAWA, J ;

KAWABATA, N ;

NISHIMUR.J .

TETRAHEDRON, 1968, 24 (01) :53-&

[6] A NOVEL ROUTE TO CYCLOPROPANES FROM OLEFINS [J].

FURUKAWA, J ;

KAWABATA, N ;

NISHIMURA, J .

TETRAHEDRON LETTERS, 1966, (28) :3353-+

[7]

FURUKAWA J, 1969, TETRAHEDRON, V25, P2647

[8]

HORTON PA, 1994, J AM CHEM SOC, V11, P6015

[9] SYNTHESIS OF METHYL 2,4,6-TRI-O-BENZYL ALPHA D-GLUCOPYRANOSIDE [J].

KOTO, S ;

TAKEBE, Y ;

ZEN, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (01) :291-+

[10] REACTIONS ON METHYL 2-DEOXY-2-TRIFLUOROACETAMIDO-3-O-TRIFLUOROMETHYLSULFONYL-ALPHA-D-GLUCOPYRANOSIDE DERIVATIVES - FORMATION OF RING-CONTRACTION COMPOUNDS [J].

TSUCHIYA, T ;

AJITO, K ;

UMEZAWA, S ;

IKEDA, A .

CARBOHYDRATE RESEARCH, 1984, 126 (01) :45-60