Total synthesis of lyngbyabellin A, a potent cytotoxic metabolite from the marine cyanobacterium Lyngbya majuscula

✍ Scribed by Fumiaki Yokokawa; Hirofumi Sameshima; Takayuki Shioiri

• Book ID: 104230744
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 138 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00678-5

✦ Synopsis

The first total synthesis of lyngbyabellin A, a novel peptolide from the marine cyanobacterium Lyngbya majuscula, is described. Both functionalized thiazole carboxylic acid units were synthesized using our CMD (chemical manganese dioxide) oxidation from the corresponding thiazolidines. The asymmetric synthesis of the dichlorinated b-hydroxy acid was achieved by the chiral oxazaborolidinone mediated aldol reaction. Finally, fragment condensation followed by the macrolactamization provided lyngbyabellin A.