Baris Temelli

Scalable Total Synthesis of (−)-Berkelic Acid by Using a Protecting-Group-Free Strategy†

Supply chain: the polycyclic core of (-)-berkelic acid (1) was constructed in just one step from very simple starting materials. The total synthesis of 1 involves a seven-step linear sequence. Protection/deprotection steps were avoided and all but the last step were performed on a gram scale. This synthesis could solve the supply problem associated with the exhaustion of the natural source.

Access to pyrrole-based heterocyclic compounds via addition of pyrrole to C=C and C=N bonds

Abstract A series of metal triflate-catalyzed addition reactions of pyrrole to C=C and C=N bonds have been investigated to access pyrrole-based heterocyclic compounds. The addition of pyrrole to different α,β-unsaturated compounds or N-tosyl imines afforded suitable structures for the construction of [5-5] bicyclic systems or porphyrins, respectively. Intramolecular cyclization reactions were applied for the synthesis of pyrrolizine derivatives. In the other reaction mode, intermolecular cyclization reactions gave A4- and trans-A2B2-meso-substituted porphyrins under mild reaction conditions with low scrambling.

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

The preparation of β-meso directly linked porphyrin–corrole hybrids was realized for the first time via an InCl3-catalyzed condensation reaction of 2-formyl-5,10,15,20-tetraphenylporphyrins with meso-substituted dipyrromethanes. Hybrid compounds have been characterized by 1H NMR, 13C NMR, 2D NMR, UV–vis absorption and fluorescence spectroscopy.

A facile synthesis and characterization of the novel 2,2-dichloro-1-[3-(2,2-dichloro-acetyl)-2-(4-methoxy-phenyl)-imidazolidin-1-yl]- ethanone

ABSTRACT The synthesis of (2,2-dichloro-1-[3-(2,2-dichloro-acetyl)-2-(4-methoxy-phenyl)-imidazolidin-1-yl]-ethanone by a facile one-pot reaction between N,N′-bis(4-methoxy-benzylidene)-ethane-1,2-diamine and dichloroacetyl chloride is described. The structure was confirmed by 1H NMR, MS and FTIR techniques and X-ray crystallography.

Unexpected formation of β, meso-directly linked diporphyrins under Adler–Longo reaction conditions

Abstract Unexpected formation of β, meso-directly linked diporphyrin products has been described in the reactions of β-formyl porphyrins with pyrrole under Adler–Longo reaction conditions. Preliminary mechanistic studies indicates that β-dipyrromethane substituted porphyrin structure is the crucial intermediate for the formation of diporphyrin product. Graphical Abstract