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Concise asymmetric synthesis of a model compound, (4S,5S,6S)-6-(2,2-dimethoxy)ethyl-4,5-epoxy-6-hydroxy-2-cyclohexenone, for the cyclohexenone core of scyphostatin

✍ Scribed by Hiromichi Fujioka; Naoyuki Kotoku; Yoshinari Sawama; Yasushi Nagatomi; Yasuyuki Kita


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
90 KB
Volume
43
Category
Article
ISSN
0040-4039

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Towards a total synthesis of ustiloxins
✍ Craig A. Hutton; Jonathan M. White πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 194 KB

A short, stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline (8), an unusual amino acid component of ustiloxins A & B, has been achieved. Stereoselective bromolactonisation of N-Boc-(S)-allylglycine (3) is followed by substitution of the bromide 4a with thiophenol to give th