Determination of the relative and absolute stereochemistry of fostriecin (CI-920)

被引：69

作者：

Boger, DL ^{[1
]}

Hikota, M ^{[1
]}

Lewis, BM ^{[1
]}

机构：

[1] Scripps Res Inst, SKAGGS INST CHEM BIOL, LA JOLLA, CA 92037 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 06期

关键词：

D O I：

10.1021/jo962166h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.

引用

页码：1748 / 1753

页数：6

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