222425-48-1Relevant articles and documents
Enantioselective synthesis of (-)-indolizidine 167B
Chalard, Pierre,Remuson, Roland,Gelas-Mialhe, Yvonne,Gramain, Jean-Claude,Canet, Isabelle
, p. 1661 - 1664 (1999)
The enantioselective total synthesis of (-)-indolizidine 167B is described. The key step is the intramolecular cyclization of the chiral N- acyliminium ion 6. Indolizidine 167B was obtained in 7 steps and 17% yield from ethyl (R)-3-aminohexanoate, with an
Isolation and Structure Determination of Lyngbyastatin 3, a Lyngbyastatin 1 Homologue from the Marine Cyanobacterium Lyngbya majuscula. Determination of the Configuration of the 4-Amino-2,2-dimethyl-3-oxopentanoic Acid Unit in Majusculamide C, Dolastatin 12, Lyngbyastatin 1, and Lyngbyastatin 3 from Cyanobacteria
Williams, Philip G.,Moore, Richard E.,Paul, Valerie J.
, p. 1356 - 1363 (2007/10/03)
The structure of lyngbyastatin 3 (1), including the configurations of the two unusual amino acid residues, viz., the 3-amino-2-methylhexanoic acid (Amha) and 4-amino-2,2-dimethyl-3-oxopentanoic acid units (Ibu), has been established by chemical degradation. Analysis of the cyanobacterial samples of lyngbyastatin 3 (1), lyngbyastatin 1 (2), and dolastatin 12 (3) demonstrated that they are mixtures of Ibu epimers [R (major) and S (minor)], whereas the structurally related majusculamide C (4) is a single diastereomer having an S-Ibu unit.