416898-38-9Relevant academic research and scientific papers
Thio-Claisen rearrangement used in preparing anti-β-functionalized γ,δ-unsaturated amino acids: Scope and limitations
Liu, Zhihua,Mehta, Sukeshi J.,Lee, Kwang-Soo,Grossman, Bryan,Qu, Hongchang,Gu, Xuyuan,Nichol, Gary S.,Hruby, Victor J.
, p. 1289 - 1300 (2012/04/10)
Multifunctionalized amino acids, especially amino acids with unsaturation, are important, demanding building blocks in peptide chemistry. Here we present a summary of our most recent study using the thio-Claisen rearrangement for the synthesis of anti-β-f
Asymmetric eschenmoser-claisen rearrangement for anti-β-substituted γ,δ-unsaturated amino acids
Qu, Hongchang,Gu, Xuyuan,Liu, Zhihua,Min, Byoung J.,Hruby, Victor J.
, p. 3997 - 4000 (2008/02/11)
Optically active anti-β-substituted γ,δ-unsaturated amino acids are important synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.
Asymmetric total syntheses of marine cyclic depsipeptide halipeptins A-D
Yu, Shouyun,Pan, Xianhua,Ma, Dawei
, p. 6572 - 6584 (2008/09/16)
Halipeptins A-D (1a-d) are a family of natural cyclic depsipeptides isolated from marine sponges. Total syntheses of these four compounds are detailed in this report. The key elements in this synthesis include the elaboration of the polysubstituted decanoic acid parts by two asymmetric aldol reactions, assembly of the N-methyl-δ-hydroxyisoleucine residue by using either aza-Claisen rearrangement or methylation of aspartates as the key steps, and macrocyclization at the polysubstituted decanoic acid alanine site.
Total synthesis and determination of the stereochemistry of 2-amino-3-cyclopropylbutanoic acid, a novel plant growth regulator isolated from the mushroom Amanita castanopsidis Hongo
Morimoto, Yoshiki,Takaishi, Mamoru,Kinoshita, Takamasa,Sakaguchi, Kazuhiko,Shibata, Kozo
, p. 42 - 43 (2007/10/03)
The unknown stereostructure of 2-amino-3-cyclopropylbutanoic acid 1, a novel plant growth regulator isolated from the mushroom Amanita castanopsidis Hongo, was determined to be (2S,3S)-2 through its racemic and enantioselective syntheses employing the che
