A practical synthesis of the cyclohexyl part of the immunosuppressant FK506

被引：2

作者：

Haller, BU ^{[1
]}

Kruber, S ^{[1
]}

Maier, ME ^{[1
]}

机构：

[1] Univ Halle Wittenberg, Fachbereich Chem, Inst Organ Chem, D-4010 Halle, Germany

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1998年 / 340卷 / 07期

关键词：

D O I：

10.1002/prac.19983400710

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Starting from the benzylidene lactone 3 of D-(-)-quinic acid the cyclohexyl fragment 15 (C-28-C-34 part) of the immunosuppressant FK506 was synthesized. Key steps include homolytic deoxygenation reactions on compounds 4 and 6 as well as a regioselective opening of the benzylidene acetal 5. Opening of the lactone 7 to provide the methyl ester 8 was followed by methylation of the hydroxy group to give 9. Further steps provided the aldehyde 12 which was elongated to the alkyne 15. This sequence provides 15 in gram quantities.

引用

页码：656 / 661

页数：6

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