Simplification of antitumoral phenanthroindolizidine alkaloids: Short synthesis of cytotoxic indolizidinone and pyrrolidine analogs

J Miguélez, A Boto, R Marin, M Diaz

Index: Miguelez, Javier; Boto, Alicia; Marin, Raquel; Diaz, Mario European Journal of Medicinal Chemistry, 2013 , vol. 66, p. 540 - 554

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Citation Number: 7

Abstract

Abstract Hydroxylated seco-analogs of cytotoxic phenanthroindolizidine alkaloids were prepared in good yields from inexpensive 4-hydroxyproline derivatives, in just two steps. Thus, a sequential oxidative radical scission–oxidation was used for the direct conversion of the proline derivative into a 2-(2-aryl-oxoethyl) pyrrolidine with a variety of aryl and heteroaryl groups. The 4R-stereogenic center allowed ready isomer separation, and ...