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Studies towards the total synthesis of rapamycin: A convergent and stereoselective synthesis of the C22C32 carbon framework

✍ Scribed by James C. Anderson; Steven V. Ley; Stephen P. Marsden

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 304 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73057-7

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✦ Synopsis

Abrfmcf: A convergent synthesis of the C22-C32 ption of rapamycin has been achieved by way of a Nozaki-Kishi coupling of vinyl iodide 14 with aldehydc 13. This aldehyde is available by the stereoselective addition of organometallic reagents to aldehyde 5, synthesised by either of two selenium mediated electrophilic cyclisations.

Optically active starting materials for this synthesis are prepared by sn enzymatic acylation of mcso-diol6.

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