Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

• Santanu Hati,
• Ulrike Holzgrabe and
• Subhabrata Sen

Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162

• oxidative dehydrogenation in the synthesis of β-carboline natural products norharmine (111), harmane (112) and eudistomin U (113) [101]. The general synthetic scheme involved the synthesis of the respective tetrahydro-β-carboline precursors of the said natural products by Pictet–Spengler reaction of

An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y

• Suresh Babu Meruva,
• Akula Raghunadh,
• Raghavendra Rao Kamaraju,
• U. K. Syam Kumar and
• P. K. Dubey

Beilstein J. Org. Chem. 2014, 10, 471–480, doi:10.3762/bjoc.10.45

• dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids. Keywords: Bischler–Napieralski reaction; dihydro-β-carboline derivatives; dihydro

• -eudistomin; eudistomin; keto amide; oxidative amidation; Introduction β-Carboline alkaloids [1] are widespread in plants, animals and some are formed naturally in the biological system. Rinehart et al. [2] reported the isolation of β-carboline alkaloids such as eudistomins [3] and several of its analogues

• from the active Caribbean colonial tunicate Eudistoma olivaceum. β-Carboline alkaloids bearing a substituted phenylacetyl group at C-1 position such as eudistomin T (1) [4], eudistomin R (2a) and eudistomin S (2b) [5] were isolated by Cardellina et al. [6], and these compounds exhibit antimicrobial