Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: Effects of the bulky protecting groups to enforce facial selectivity

被引：80

作者：

Choi, WJ ^{[1
]}

Moon, HR ^{[1
]}

Kim, HO ^{[1
]}

Yoo, BN ^{[1
]}

Lee, JA ^{[1
]}

Shin, DH ^{[1
]}

Jeong, LS ^{[1
]}

机构：

[1] Ewha Womans Univ, Coll Pharm, Med Chem Lab, Seoul 120750, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 07期

关键词：

D O I：

10.1021/jo0356762

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.

引用

页码：2634 / 2636

页数：3

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