AN ALTERNATIVE ACCESS TO (+/-)-ALPHA-IRONES AND (+/-)-BETA-IRONE VIA ACID-MEDIATED CYCLIZATION

被引：9
作者：
SCHULTEELTE, KH [1 ]
PAMINGLE, H [1 ]
UIJTTEWAAL, AP [1 ]
SNOWDEN, RL [1 ]
机构：
[1] FIRMENICH CO,RES LABS,POB 239,CH-1211 GENEVA 8,SWITZERLAND
来源：
HELVETICA CHIMICA ACTA | 1992年 / 75卷 / 03期
关键词：
D O I：
10.1002/hlca.19920750312
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Acid-mediated cyclisation of trienone 8, readily available from 2,3-dimethylbutanal (1; five steps: 47% yield), using fluorosulfonic acid (6-8 mol-equiv.) in 2-nitropropane at -70-degrees, afforded a 14:9:1 mixture (70% yield) of (+/-)-cis-alpha-irone (9), (+/-)-trans-alpha-irone (10), and (+/-)-beta-irone (11). Other acidic conditions examined, using 95% aq. H2SO4 solution, 85% aq. H3PO4 solution, or SnCl4, gave inferior results.
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页码：759 / 765
页数：7
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