Synthetic studies on heterocyclic natural products.
This article reviews past and ongoing research in the author's laboratory directed toward the synthesis of natural products displaying an azaspirocyclic framework, or incorporating a medium-ring nitrogen heterocycle. New synthetic technologies were devised in order to address the synthetic problems posed by the target molecules. Thus, efforts in the area of azaspirocyclic substances have relied on an oxidative amidation of phenols promoted by iodobenzene diacetate, whereas access to medium-ring nitrogen heterocycles has been secured by means of a ring expansion sequence that relies on the fragmentation of an aziridine triggered by a homo-Brook transposition. Details of the development of these technologies are presented, together with applications to the total synthesis of FR-901483, TAN-1251C, cylindricines, and mitomycinoids.
Ciufolini
Marco A
MA
Laboratoire de Synthèse et Méthodologie Organiques (LSMO), Université Claude Bernard Lyon 1 et Ecole Supérieure de Chimie, Physique, Electronique de Lyon, 43, Boulevard du 11-Novembre-1918, 69622 Villeurbanne cedex, France. ciufi@chem.ubc.ca
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001372:Aza Compounds; D006571:Heterocyclic Compounds; D009943:Organophosphorus Compounds; D013141:Spiro Compounds; D009584:Nitrogen