110579-36-7Relevant articles and documents
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.
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).