Total synthesis and biological evaluation of halipeptins A and D and analogues

…, DA Longbottom, M Rodriquez, M Bucci…

Index: Nicolaou; Lizos, Dimitrios E.; Kim, David W.; Schlawe, Daniel; De Noronha, Rita G.; Longbottom, Deborah A.; Rodriquez, Manuela; Bucci, Mariarosaria; Cirino, Giuseppe Journal of the American Chemical Society, 2006 , vol. 128, # 13 p. 4460 - 4470

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Citation Number: 56

Abstract

The marine-derived halipeptins A (1a) and D (1d) and their analogues 3a, 3d and 4a, 4d were synthesized starting from building blocks 10, 13, 14a or 14d, 15, and 16. The first strategy for assembling the building blocks, involving a macrolactamization reaction to form the 16-membered ring hydroxy thioamide 52d as a precursor, furnished the epi-isoleucine analogue (4d) of halipeptin D, whereas a second approach involving thiazoline formation ...

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