Total synthesis of a monocyclic analogue of compactin

✍ Scribed by Mikhail S. Ermolenko; Alain Olesker; Gabor Lukacs

• Book ID: 104215565
• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 238 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75798-4

✦ Synopsis

Total synthesis of Knranertsky's monocyclic Compactin anafogue 4 has been m2ornplished In the preceeding Letterl, we have described the stereoselective synthesis of the aldehyde 1, the cyclohexane core of a new semi-synthetic HMG-CoA reductase inhibitor 4 2. Since related aldehydes have already been used in the synthesis of mevinic acids 3, the synthesis of 4 might be considered as formally completed. However, the acetaldehyde type spacer chain in 1 offers other possibilities for the construction of the lactone portion of 4. One of thase (route a), although devoided of stereochemical restrictions at the C-C bond forming step4. had some inhcrcnt disadvantages: the reagent 2 (M = SnBu3) required a multistcp synthesis and the overall yield was modest. Howcvcr. the C-glycosidation method (route b) afforded the lactonc 4 in a straightforward manner (Scheme 1). 0 /&I5 .__.._-_..