Zanoni Giuseppe, Porta Alessio, Castronovo Francesca, Vidari Giovanni
Department of Organic Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, Italy.
J Org Chem. 2003 Jul 25;68(15):6005-10. doi: 10.1021/jo034658h.
A stereoselective Julia-Lythgoe olefination followed by an efficient 1,3-allylic transposition of the C-9 hydroxyl group of compound 13 has allowed the first total synthesis of J(2) isoprostane (1), a recently discovered member of the growing isoprostane family. This elusive compound opens up numerous new avenues for the molecular biology of cyclopentenone prostaglandins which are endowed of intriguing biological effects such as antitumor, antiinflammatory, and antiviral activities. In principle, our approach is flexible enough to allow an easy synthesis of other isoprostanes of the J family following the same methodology.
通过立体选择性的Julia-Lythgoe烯化反应，随后对化合物13的C-9羟基进行高效的1,3-烯丙基迁移，首次全合成了J(2)异前列腺素(1)，它是最近在不断增加的异前列腺素家族中发现的成员。这种难以捉摸的化合物为环戊烯酮前列腺素的分子生物学开辟了许多新途径，环戊烯酮前列腺素具有诸如抗肿瘤、抗炎和抗病毒活性等有趣的生物学效应。原则上，我们的方法足够灵活，能够按照相同的方法轻松合成J家族的其他异前列腺素。
