Studies on the Novel Cyclodepsipeptides. A Total Synthesis of (+)-Jasplakinolide (Jaspamide)

Abstract

Diastereocontrolled total synthesis of (+)-jasplakinolide (1) has been accomplished via coupling of the tetrapropionate-derived segment (9) with the tripeptide (10) followed by trichlmbemyl chloride-mediated macrolactonization.(+)-Jasplakinolide (Jaspamide) ( I ) ~ and (+)-geodiamolides A (2) -F (7)4 are biologically active cyclodepsipeptides isolated from marine sponges, and are composed of hipeptides linked to a common twelve-carbon segment.With their isolation and elucidation of their smctures having been reported, synthetic work has appeared successively~ As one of the results reported, we exhibited a design for (+)-geodiamolides A (2) and B (3). consisting of the synthesis of the tetrapropionate-derived segment (9) and of the tripeptide containing a halogenated N-methyltyrosyl residue and subsequent coupling of them5e We describe here the application of this methodology to a total synthesis of (+)-jasplakinolide (1)