Utilization of a Michael addition: dipolar cycloaddition cascade for the synthesis of (+/-)-cylindricine C.
A new approach to the marine alkaloid (+/-)-cylindricine C has been devised. The key element of the synthesis consists of a Michael addition/dipolar cycloaddition cascade between 2,3-bis(phenylsulfonyl)-1,3-butadiene and 9-triisopropylsilanyloxy-non-1-en-5-one oxime. The resulting cycloadduct was converted into (+/-)-cylindricine C by a sequence of reactions including a reductive cyclization, intramolecular enolate alkylation, and conjugate addition to introduce the n-hexyl side chain.
Flick
Andrew C
AC
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
Caballero
Maria José Arevalo
MJ
Padwa
Albert
A
D000478:Alkylation; D000818:Animals; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D014561:Urochordata / Q000737:chemistry
D006575:Heterocyclic Compounds, 3-Ring; D015363:Quinolones; C485391:cylindricine C