Synthesis of C-2 functionalised 1,6,8-trioxadispiro[4.1.5.3]pentadec-13-enes

被引：17

作者：

Allen, PR ^{[1
]}

Brimble, MA ^{[1
]}

Fares, FA ^{[1
]}

机构：

[1] Univ Sydney, Sch Chem, Camperdown, NSW 2006, Australia

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 15期

关键词：

D O I：

10.1039/a802490a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of bis-spiroacetals 28 and 44, model systems for the tricyclic bis-spiroacetal moiety of the polyether antibiotic epi-17-deoxy-(O-8)-salinomycin 3, are described. Introduction of an aldehyde group at C-2 was necessary for further elaboration of the right hand side of the molecule. It was found that the choice of protecting group on the hydroxymethyl substituent (precursor to an aldehyde group) was crucial to the outcome of the key oxidative cyclisation.

引用

页码：2403 / 2411

页数：9

共 19 条

[1] CHEMISTRY OF BIS-SPIROACETALS - SYNTHESIS OF CIS-1-(2-METHYL-1,6,8-TRIOXADISPIRO[4.1.5.3]PENTADEC-13-EN-2-YL)METHANOL AND TRANS-1-(2-METHYL-1,6,8-TRIOXADISPIRO[4.1.5.3]PENTADEC-13-EN-2-YL)METHANOL
BRIMBLE, MA
WILLIAMS, GM
BAKER, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09): : 2221 - 2227
[2] SYNTHESIS OF THE BIS-SPIROACETAL MOIETY OF 17-EPI-20-DEOXYSALINOMYCIN
BRIMBLE, MA
WILLIAMS, GM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5818 - 5822
[3] BROWN RCD, 1994, SYNLETT, P415
[4] BROWN RCD, 1994, SYNLETT, P417
[5] HORITA K, 1989, CHEM PHARM BULL, V37, P1698
[6] HORITA K, 1989, CHEM PHARM BULL, V37, P1705
[7] HORITA K, 1989, CHEM PHARM BULL, V37, P1717
[8] HORITA K, 1989, CHEM PHARM BULL, V37, P1726
[9] NOBORITOMYCIN-A AND NOBORITOMYCIN-B NEW POLYETHER ANTIBIOTICS
KELLERJUSLEN, C
KING, HD
KUHN, M
LOOSLI, HR
WARTBURG, AV
[J]. JOURNAL OF ANTIBIOTICS, 1978, 31 (09) : 820 - 828
[10] KINASHI H, 1973, TETRAHEDRON LETT, P4955

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