Thominet Olivier, Baker James R, Britton Hugh, Etheridge Zac C, Soscia Marco G, Caddick Stephen
Department of Chemistry, University College London, 20 Gordon Street, London, UK.
Org Biomol Chem. 2007 Nov 21;5(22):3703-12. doi: 10.1039/b711196g. Epub 2007 Oct 3.
We present herein our recent efforts towards the synthesis of epoxydiynes which represent an unusual structural feature of the neocarzinostatin chromophore. A number of different routes to these epoxydiynes have been explored with varying success. Ultimately a concise and convergent approach was developed, which involved the addition of an allenyl zinc bromide to propargylic ketones/aldehydes followed by epoxide formation. This new protocol enabled us to synthesise a fully elaborated epoxydiyne which will find application for our studies towards the total synthesis of the NCS chromophore.
在此，我们展示了近期在合成环氧二炔方面所做的努力，环氧二炔代表了新制癌菌素发色团的一种独特结构特征。我们探索了多种不同的合成这些环氧二炔的路线，取得了不同程度的成功。最终开发出了一种简洁且汇聚式的方法，该方法包括将烯丙基溴化锌加成到炔丙基酮/醛上，随后形成环氧化物。这种新方法使我们能够合成一种结构完全明确的环氧二炔，它将应用于我们对新制癌菌素发色团全合成的研究中。
