Synthetic studies on stevastelins. 1. Total synthesis of stevastelins B and B3.
[Chemical reaction: See text] The synthesis of stevastelin B3 (2) and B (5) are described. In a first approach, epoxy cyclodepsipeptide 8 was considered as a promising candidate for the synthesis of the [15]-membered ring members of the stevastelins; however, the oxirane ring opening, required for the completion of the natural stevastelin synthesis, failed. Thus, we synthesized stevastelin B (5), carrying out the oxirane ring opening earlier in the synthesis and following a synthetic scheme capable of delivering analogues. On the other hand, a translactonization reaction of the [15]-membered ring derivative 59 led to the total synthesis of the natural [13]-membered ring component of the stevastelins family, stevastelin B3 (2).
Sarabia
Francisco
F
Department of Biochemistry, Molecular Biology and Organic Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071, Malaga, Spain. frsarabia@uma.es
Chammaa
Samy
S
D000596:Amino Acids / Q000737:chemistry; D047630:Depsipeptides / Q000138:chemical synthesis*; D004852:Epoxy Compounds; D005656:Fungal Proteins / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry
D000596:Amino Acids; D047630:Depsipeptides; D004852:Epoxy Compounds; D005656:Fungal Proteins; D007202:Indicators and Reagents; D010455:Peptides; C100705:stevastelin B; C100706:stevastelin B3