159360-04-0Relevant articles and documents
Total syntheses and biological investigations of tamandarins A and B and tamandarin A analog
Liang,Richard,Portonovo,Joullie
, p. 4469 - 4474 (2007/10/03)
Tamandarins A (1) and B (2), two natural products similar in structure to didemnin B (3), were recently isolated from a Brazilian marine ascidian of the family Didemnidae. The cytotoxicity of 1 was reported to be somewhat more potent in vitro than that of 3 against various human cancer cell lines. The present account describes the first total syntheses of 1 and 2, and the syntheses of tamandarin A side chain analogues. The cytotoxicity data for these compounds show that the side chain modifications exhibit a parallel effect for both didemnins and tamandarins. This observation supports tamandarins' role as didemnins' mimic.
Synthesis of D-Alloisoleucine from L-Isoleucine and from (S)-2-Methylbutan-1-ol. Synthesis of Isostatine
Lloyd-Williams, Paul,Monerris, Patricia,Gonzalez, Isabel,Jou, Gemma,Giralt, Ernest
, p. 1969 - 1974 (2007/10/02)
Three different synthetic routes to the uncommon α-amino acid D-alloisoleucine were studied.The first was based on the stereospecific inversion of configuration of the C-2 stereogenic carbon of L-isoleucine.The second involved acetylation of L-isoleucine with epimerization at the C-2 carbon, giving a mixture of L-isoleucine and D-alloisoleucine, which was resolved enzymically with hog kidney acylase.In a new approach, an epimeric mixture of L-isoleucine and D-alloisoleucine was synthesized from (S)-2-methylbutan-1-ol and was again resolved enzymically.The D-alloisoleucine produced in these syntheses was subsequently transformed into the γ-amino acid isostatine.
