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Towards a total synthesis of ustiloxins A & B. Stereocontrolled synthesis of (2S,4S,6S)-4-hydroxy-5-phenylsulfinylnorvaline

✍ Scribed by Craig A. Hutton; Jonathan M. White

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
194 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 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.

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