Cofactor regeneration; i.e., regiospecific conversion of NAD+ to 1,4-NADH, has been extensively studied and is a crucial component in the eventual use of 1,4-NADH in a variety of bioorganic synthesis processes involving the formation of chiral organic compounds. We have studied the reduction of a model NAD+ compound, 1-benzylnicotinamide triflate, 1a, using [Cp*Rh(bpy)(H2O)]2+, 2 (Cp* = η5-C5Me5, bpy = 2,2‘-bipyridyl), as the catalyst precursor and sodium formate (HCO2Na) as the hydride source in 1:1 H2O/THF and have found exclusive 1-benzyl-1,4-dihydronicotinamide regioselectivity, as was observed previously for natural NAD+ that provided 1,4-NADH (see:  Steckhan et al. Organometallics 1991, 10, 1568). Moreover, a variety of 3-substituted derivatives of 1-benzylpyridinium triflate, in addition to the −C(O)NH2 group (1a), were also studied to ascertain that this 3-functionality (e.g., −C(O)NHCH3, −C(S)NH2, −C(O)CH3, −C(O)OCH3, and −CN, 1b,d−g) coordinates to a [Cp*Rh(bpy)H]+ complex to direct the concerte...

Bioorganometallic Chemistry. 13. Regioselective Reduction of NAD+ Models, 1-Benzylnicotinamde Triflate and β-Nicotinamide Ribose-5‘-methyl Phosphate, with in Situ Generated [Cp*Rh(Bpy)H]+: Structure−Activity Relationships, Kinetics, and Mechanistic Aspects in the Formation of the 1,4-NADH Derivatives†

A Preliminary Investigation of Ibogaine. Case Reports and Recommendations for Further Study.

Publisher Summary The chapter discusses ibogaine, which is a naturally occurring plant alkaloid with a history of use as a medicinal and ceremonial agent in West Central Africa and has been alleged to be effective in the treatment of drug abuse. The National Institute on Drug Abuse (NIDA) has given significant support to animal research, and the U.S. Food and Drug Administration (FDA) has approved Phase I studies in humans. The chapter discusses the first International Conference on Ibogaine. A major focus of the Conference was the possible mechanism(s) of action of ibogaine. Another important focus of the Conference was to discuss human experience with ibogaine and preclinical and clinical evidence of efficacy and safety. The Conference also featured presentations related to the sociological and anthropological aspects of the sacramental context of the use of iboga in Africa and the distinctive ibogaine subculture of the U.S and Europe. Ibogaine is the most abundant alkaloid in the root bark of the Apocynaceous shrub Tabernanthe iboga , which grows in West Central Africa. The chapter presents a timeline that outlines the historical events relating to the development of ibogaine as a treatment for drug dependence. Ibogaine and serotonin both contain an indole ring in their structure, and ibogaine has been shown to bind to the serotonin transporter and to increase serotonin levels in the nucleus accumbens (NAc). Stereotypy is a methodologic issue that might explain some of the disparate results regarding ibogaine's interaction with the locomotor response to cocaine.

Ibogaine: a review.

The indole 2-3-quinodimethane strategy for the synthesis of indole alkaloids

A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine

P. E. Sonnet

Papers

The Total Synthesis of Iboga Alkaloids1

The Total Synthesis of (±)-Ibogamine and of (±)-Epiibogamine