Long-chain 2H-Azirines with heterogeneous terminal halogenation from the marine sponge Dysidea fragilis

被引：69
作者：
Skepper, Colin K. [1 ]
Molinski, Tadeusz F. [1 ,2 ]
机构：
[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA
[2] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92093 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 07期
关键词：
D O I：
10.1021/jo702435s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Three new omega-halogenated long-chain 2H-azirines were isolated from the sponge Dysidea fragilis. Their structures revealed heterogeneity in both the composition of the terminal 1,1-dihalo-vinyl group and enantiomeric ratios at C2 of the azirine-2-carboxylate ester terminus. Azirine-2-carboxylate esters were shown to racemize spontaneously. A hypothesis is proposed for the biosynthesis of the azirinecarboxylate family of natural products that involves enzyme-catalyzed free radical halogenation followed by elimination of hydrohalic acid.
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页码：2592 / 2597
页数：6
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