New approach to the synthesis of macrocyclic core of cytotoxic lactone ( )-neopeltolide. Synthesis of C-C segment basing on cyclopropanol intermediates.
A new retrosynthetic procedure was developed for the synthesis of the macrocyclic core of a cytotoxic lactone ( )-neopeltolide utilizing cyclopropanol intermediates. The synthesis was suggested and carried out of the C-C segment of ( )-neopeltolide to obtain (4 S,6 S)-6-[(2 S)-2-hydroxypentyl]-4-methyltetrahydro-2 H-pyran-2-one. The possibility was demonstrated of a formal synthesis based on the obtained product of the potential antitumor pharmaceutical ( )-neopeltolide.