Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent: Leading to Galanthamine-Type Amaryllidaceae Alkaloids
The Journal of Organic Chemistry1998Vol. 63(19), pp. 6625–6633
Citations Over TimeTop 1% of 1998 papers
Yasuyuki Kita, Mitsuhiro Arisawa, Michiyo Gyoten, Makiko Nakajima, Ryuji Hamada, Hirofumi Tohma, Takeshi Takada
Abstract
By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (±)-sanguinine and the total syntheses of (±)-galanthamine, (±)-narwedine, (±)-lycoramine, and (±)-norgalanthamine were also successfully carried out.
Related Papers
- → A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2H-azirines(2019)31 cited
- → Alternative Strategies with Iodine: Fast Access to Previously Inaccessible Iodine(III) Compounds(2018)30 cited
- → Improved Method for the Iodine(III)-Mediated Preparation of Aryl Sulfonimidates(2005)29 cited
- → The nature of iodine oxygen bonds in hypervalent 10-I-3 iodine compounds(2004)13 cited
- → ChemInform Abstract: m‐Iodosylbenzoic Acid as a Convenient Recyclable Hypervalent Iodine Oxidant for the Synthesis of α‐Iodo Ketones by Oxidative Iodination of Ketones.(2011)