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首页> 外文期刊>Chemistry: A European journal >Total synthesis of amiclenomycin, an inhibitor of biotin biosynthesis
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Total synthesis of amiclenomycin, an inhibitor of biotin biosynthesis

机译：生物素生物合成抑制剂阿莫霉素的全合成

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摘要

We describe the first synthesis of amiclenomycin, a natural product that has been found to inhibit biotin biosynthesis and, as a consequence to exhibit antibiotic properties. Structure 1, with a trans relationship between the ring substituents, had previously been proposed for amiclenomycin on the basis of its ~1H NMR spectrum. We have prepared the trans and cis isomers 1 and 2 by unequivocal routes and we conclude that the natural product is in fact the cis isomer 2. The properly substituted cyclohexadienyl rings were constructed first. A cycloaddition reaction between 1,2-di(phenylsulfonyl)ethylene and the N-allyloxycarbonyl diene 13, followed by reductive elimination of the phenylsulfinyl groups, gave the cis isomer 15. To obtain the trans isomer, the O-trimethylsilyl diene was used to give the cis hydroxylated Diels-Alder adduct 33, which was transformed into the corresponding trans amino derivative by means of a Mitsunobu reaction. The L-#alpha#-amino acid functionality was introduced by means of a Strecker reaction on the aldehydes 16 and 42, followed by enzymatic hydrolysis withimmobilised pronase.
机译：我们描述了氨苄菌素的首次合成，氨苄菌素是一种天然产物，已被发现抑制生物素的生物合成，并因此表现出抗生素特性。先前已经基于氨苄菌素的〜1H NMR光谱提出了具有环取代基之间的反式关系的结构1。我们已经通过明确的途径制备了反式和顺式异构体1和2，并且得出结论，天然产物实际上是顺式异构体2。首先构建了适当取代的环己二烯基环。在1,2-二（苯磺酰基）乙烯与N-烯丙氧基羰基二烯13之间进行环加成反应，然后还原性消除苯基亚磺酰基，得到顺式异构体15。为了获得反式异构体，使用O-三甲基甲硅烷基二烯得到顺式羟基化的Diels-Alder加合物33，其通过Mitsunobu反应转化为相应的反氨基衍生物。通过在醛16和42上的Strecker反应引入L-＃α＃-氨基酸官能度，然后用固定化的链霉蛋白酶进行酶促水解。

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