Synthesis of (1'S,3'R)-3-(3'-amino-2',2'-dimethylcyclobutyl)propan-1-ol from (-)-beta-pinene

被引：0
|
作者：
Blanco, JM
Caamano, O
Fernandez, F
Gomez, G
Nieto, I
机构：
[1] UNIV SANTIAGO,FAC FARM,DEPT QUIM ORGAN,E-15706 SANTIAGO,SPAIN
[2] UNIV VIGO,EUITI,DEPT QUIM PURA & APLICADA,E-36208 VIGO,SPAIN
来源：
SYNTHESIS-STUTTGART | 1996年 / 02期
关键词：
(-)-beta-pinene; (+)-nopinone; Beckman rearrangement; hydroxylamine-O-sulfonic acid; carbocyclic nucleosides;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The title compound 3, a useful intermediate in the synthesis of carbocyclic analogs of nucleosides was synthesized from (-)-beta-pinene (4) in seven steps: oxidation of 4 to (+)-nopinone (5); Beckmann rearrangement of the oxime-O-sulfonic acid of 5 to the bicyclic lactam 7 (a two-step procedure via oxime 6 is also described); hydrolytic ring opening of 7 to form amino acid HCl 8; and reduction of the corresponding protected methyl ester 10 followed by deprotection. Overall yield, 67% from lactam 7.
引用
收藏
页码：281 / &
页数：5
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