A facile synthesis of (−)- and (+)-Geissman–Waiss lactone via intramolecular Rh(II)-carbenoid mediated C–H insertion reaction: synthesis of (1R,7R,8R)-turneforcidine

✍ Scribed by Andrew G.H Wee

• Book ID: 104211213
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 70 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01664-6

✦ Synopsis

The intramolecular C-H insertion reaction in chiral non-racemic diazoacetates (-)-6 and (+)-8 catalyzed by chiral Rh 2 (MPPIM) 4 proceeded efficiently, with excellent regioselectivity and cis-diastereoselectivity, to give (-)-and (+)-Geissman-Waiss lactone, 4b, respectively. Bicyclic lactone (-)-4b was used in the synthesis of the necine base (-)-turneforcidine 3.