Synthesis of a Key Building Block for a Butyrolactone → 1,3-Diol Approach to the Polyol Part of Roflamycoin

✍ Scribed by Diego Muñoz-Torrero; Reinhard Brückner

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 714 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199806)1998:6<1031::aid-ejoc1031>3.0.co;2-d

✦ Synopsis

For preparing tris(γ-lactone) 3 the mono(γ-lactone) 6 was synthesized from the dichlorodiol 12 (99.8% ee). Bisepoxide 9 -derived from dichlorodiol 12 (99.8% ee) -was ringopened with the Gilman cuprate from 2-lithio-1,5-hexadiene and CuI giving almost exclusively the monoepoxide 21; in five more steps, γ-lactone 30 with the same stereotriad as the target molecule 6 but a different protecting group was