合成氟维菌素B2 - B5、Sch 38518和Sch 39185的有效方法。通过交叉复分解（CM）和关环复分解（RCM）反应首次合成它们的苷元。
Efficient approach to fluvirucins B2-B5, Sch 38518, and Sch 39185. First synthesis of their aglycon, via CM and RCM reactions.
作者信息
Llàcer Enric, Urpí Fèlix, Vilarrasa Jaume
机构信息
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Av. Diagonal 647, 08028 Barcelona, Catalonia, Spain.
出版信息
Org Lett. 2009 Aug 6;11(15):3198-201. doi: 10.1021/ol901030f.
A route to fluvirucinins B(2-5) (the common aglycon of fluvirucins B(2)-B(5), Sch 38518, and Sch 39185) is reported for the first time. A ring-closing metathesis (RCM) generated the C6-C7 double bond, which by catalytic hydrogenation (in toluene) gave the desired epimer with a 9:1 diastereoselection. Azide 8a and carboxylic acid 5 came from ethyl-branched fragments C9-C13 (CHO at C9) and C1-C5 via an asymmetric allylation of the former and a cross metathesis (CM) followed by a ketone methylenation (with 20 mol % of DMF as a sacrificial additive) of the latter.
首次报道了一条合成氟维菌素B(2 - 5)（氟维菌素B(2)-B(5)、Sch 38518和Sch 39185的共同苷元）的路线。关环复分解反应（RCM）生成了C6 - C7双键，该双键通过催化氢化（在甲苯中）以9:1的非对映选择性得到所需的差向异构体。叠氮化物8a和羧酸5分别来自乙基支链片段C9 - C13（C9位为醛基）和C1 - C5，前者通过不对称烯丙基化反应，后者通过交叉复分解反应（CM），然后进行酮亚甲基化反应（以20 mol%的DMF作为牺牲添加剂）得到。
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