Asymmetric Synthesis of (+)-Tanikolide and the β-Methyl-Substituted Analogues of (+)-Tanikolide and (-)-Malyngolide

• Published in: European Journal of Organic Chemistry Vol. 2011; no. 35; pp. 7097 - 7106
• Main Authors: Doran, Robert, Duggan, Lesley, Singh, Surrendra, Duffy, Colm D., Guiry, Patrick J.
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-12-2011; WILEY‐VCH Verlag
• Subjects: Asymmetric synthesis; Lactones; Natural products; Zirconium
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201101190

The δ‐lactone‐containing natural product (+)‐tanikolide, a brine shrimp toxin and antifungal compound, was synthesized in nine steps with an overall yield of 26.4 % by employing Sharpless asymmetric epoxidation and ZrCl4‐catalyzed intramolecular acetalization as the key steps. The novel β‐methyl‐substituted analogues of (+)‐tanikolide and(–)‐malyngolide have also been prepared by using the same asymmetric synthetic approach.
The marine antifungal (+)‐tanikolide was synthesized in overall 26.4 % yield along with the β‐methyl‐substituted tanikolide and malyngolide analogues by usingSharpless asymmetric epoxidation and ZrCl4‐catalyzed cyclic acetal formation as key steps.