The synthesis of epoxypiperolides and piperolides

✍ Scribed by Andrew Pelter; Redha Al-Bayati; Pushpa Pardasani

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 177 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)84091-5

✦ Synopsis

A general synthesis of alkynyl orthoesters leads to intermediates that couple with 2-trimethylsilyloxy-4-methoxyfuran to give compounds from which epoxypiperolide and isomers are available as well as all piperolide isomers.

Piperolide II, epoxypiperolide 2 1a,2 and (-)-threo-7,8-dihydroxypiperolide, 3 3 are

«r: 8 unfortunately goes in a 1,4-fashion entirely. However, 16 itself condenses with 8 to rv «r: rv give 18 (77%) which is readily reduced to pure. recrystallised 19, a key compound. in 80% 'V'v 'V'v yield. c _ _-'.~PhC,C.C(OMeh ----1.~PhCH:CH.C(OMe)3 'V, 'VI, 'V,

provided with a plethora of labile functionality ready for rearrangements. For example, 'VV';