Synthesis of Jasplakinolide Analogues Containing a Novel ω‐Amino Acid.

Abstract

Synthesis of Jasplakinolide Analogues Containing a Novel ω-Amino Acid. -The novel amino acid (III) incorporates conformational constraints due to non-bonded interactions. It is part of cyclodepsipeptide analogues (I) and (II) of geodiamolide A. Whereas (I) are devoid of any cytotoxic effects, weak activity is observed for (IIa) and a moderate one for (IIb). -(MARIMGANTI, S.; YASMEEN, S.; FISCHER, D.; MAIER*, M. E.; Chem. Eur. J. 11 (2005) 22, 6687-6700; Inst. Org. Chem., Eberhard-Karls-Univ., D-72076 Tuebingen, Germany; Eng.) -Klein 15-185

New Structures and Bioactivity Properties of Jasplakinolide (Jaspamide) Analogues from Marine Sponges

“…Some of these schemes have been used to prepare small sets of analogues for structure activity relationship studies, but none have shown biological activity on a par with that of 1 . Highlights of the deleterious changes include inserting amino acids into the polyketide synthase (PKS) segment and replacing the methyl groups at C-13/C-15 33, 34. Similarly, total synthesis of 2 and three non-natural diastereomers revealed the sensitivity of cytotoxic action against solid tumors35 and relative ability to induce actin polymerization to changes in configurations of substituents on the polyketide portion of the molecular framework.…”