110579-36-7Relevant academic research and scientific papers
Towards a total synthesis of ustiloxins A and B. Stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline
Hutton, Craig A.,White, Jonathan M.
, p. 1643 - 1646 (2007/10/03)
A short, stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline (8), an unusual amino acid component of ustiloxins A and B, has been achieved. Stereoselective bromolactonisation of N-Boc-(S)-allylglycine (3) is followed by substitution of the bromide 4a with thiophenol to give the corresponding sulfide 5. Highly stereoselective oxidation of the sulfide 5 gives the corresponding sulfoxide 6a. Removal of the Boc group and lactone ring opening then complete the synthesis of the unusual amino acid.
Synthetic Studies on Antifungal Cyclic Peptides, Echinocandins. Stereoselective Total Synthesis of Echinocandin D via a Novel Peptide Coupling
Kurokawa, Natsuko,Ohfune, Yasufumi
, p. 6195 - 6222 (2007/10/02)
Synthetic studies on the novel fungicidal oligopeptides, echinocandins (1b and 1c), are described.The constituent amino acids 5-8 were synthesized in a stereocontrolled manner from the chiral starting materials, 5a, 6a and 7a, respectively.The coupling of these amino acids was characterized by the use of unprotected amino acid as the C-terminal and 2-pyridyl thiol ester as the N-terminal, and the coupling was performed in the presence of 1-(trimethylsilyl)imidazole (TMSIm) or a catalytic amount of tert-amine to give C-terminal free dipeptides, 14 and 16a, respectively, which were converted to the pentapeptide 17a, a common intermediate for the synthesis of 1b and 1c.The synthesis of 1c was achieved by the cyclization of the hexapeptide 24b.
AN EFFICIENT ROUTE TO 1,3-AMINO HYDROXYL SYSTEM VIA ELECTROPHILIC LACTONIZATION OF 2-AMINO-4-PENTENOIC ACID DERIVATIVES. STEREOSELECTIVE SYNTHESIS OF (-)-BULGECININE
Ohfune, Yasufumi,Hori, Keiko,Sakaitani, Masahiro
, p. 6079 - 6082 (2007/10/02)
Several γ-hydroxy-α-amino acid systems were prepared stereoselectively from 2-amino-4-pentenoic acid derivatives using electrophilic lactonization.This strategy was applied to the synthesis of a highly functionalized proline analogue, (-)-bulgecinine (4).
