Diastereoselective zirconocene-promoted bicyclization-carbonylation of allylically methyl-substituted enynes. Synthesis of (+)-iridomyrmecin

✍ Scribed by Gilbert Agnel; Zbyslaw Owczarczyk; Ei-ichi Negishi

• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 226 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91669-1

✦ Synopsis

summaly:

Allylically methyl-substituted 1,6_heptenynes, such as 3-methyl-1,6-octenyne, can be diastereoselectively converted to the corresponding bicyclic ketones, such as (SR,6S)-2,6-dimethylbicyclo[3.3.0]oct-l-en-3one readily convertible to (+)-iridomynnecin, the observed diastereomeric excesses of the bicyclization reaction being >90%.