Studies on the Total Synthesis of Streptazolin and Its Related Natural Products: First Total Synthesis of (±)-8α-Hydroxystreptazolone
The intramolecular Pauson-Khand reaction of 2-oxazolone derivatives with a suitable heptynyl appendage gave exclusively the corresponding 4-hydroxy-6-substituted-9-oxa-1-azatricyclo[6.2.1.0 5,11]-undec-5-ene-7,10-diones. On the basis of this newly developed Pauson-Khand reaction of 2-oxazolone-alkyne derivatives, the first total synthesis of (±)-8α-hydroxystreptazolone was accomplished in a highly stereoselective manner. In addition, (±)-7-epi-8α -hydroxystreptazolone was also synthesized.
Nomura, Izumi,Mukai, Chisato
p. 1803 - 1812
(2007/10/03)
Total synthesis of (+/-)-8alpha-hydroxystreptazolone.
[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.
Nomura, Izumi,Mukai, Chisato
p. 4301 - 4304
(2007/10/03)
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