Convergent synthesis of the amphotericin polyol subunit employing asymmetric dienolate addition reactions

✍ Scribed by Jochen Krüger; Erick M. Carreira

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 268 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01467-1

✦ Synopsis

We have described a convergent asymmetric synthesis of the polyol fragment of amphotericin B that utilizes a versatile dienolate aldol addition reaction of furfural to rapidly assemble the constituent polyol subunit. This strategy allows for the efficient synthesis of large quantities of the desired fragment while being inherently flexible to allow the construction of analogs. The synthesis of the C1-CI3 fragment of amphotericin requires only eleven steps and proceeds in 28% overall yield.