Nomura Izumi, Mukai Chisato
Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920-0934, Japan.
Org Lett. 2002 Nov 28;4(24):4301-4. doi: 10.1021/ol020189e.
[reaction: see text] The intramolecular Pauson-Khand reaction of 2-oxazolone derivatives with a suitable pentynyl appendage exclusively gave the corresponding 4-hydroxy-6-substituted-9-oxa-1-azatricyclo[6.2.1.0(5,11)]undec-5-en-7,10-diones. Based on this newly developed Pauson-Khand reaction of 2-oxazolone-alkyne derivatives, the first total synthesis of (+/-)-8alpha-hydroxystreptazolone was accomplished in a highly stereoselective manner.
[反应：见正文] 具有合适戊炔基侧链的2-恶唑酮衍生物的分子内Pauson-Khand反应专一性地生成相应的4-羟基-6-取代-9-氧杂-1-氮杂三环[6.2.1.0(5,11)]十一碳-5-烯-7,10-二酮。基于这种新开发的2-恶唑酮-炔烃衍生物的Pauson-Khand反应，以高度立体选择性的方式完成了(±)-8α-羟基链霉唑酮的首次全合成。
