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Synthesis 2006(13): 2173-2182
DOI: 10.1055/s-2006-942426
DOI: 10.1055/s-2006-942426
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (2S,3R,4S)-Isonorstatine Using a Solvent-Induced Highly Stereoselective 3-Butenyl Addition to l-Threose Imines
Further Information
Received
29 May 2006
Publication Date:
12 June 2006 (online)
Publication History
Publication Date:
12 June 2006 (online)
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Abstract
Isonorstatine was obtained in an 11-step sequence starting from l-tartaric acid, based on a highly stereoselective addition of 1-butene-3-yl to a threose imine. The orientation of the methyl group at C-4 of isonorstatine was determined by transformation of the key δ-xylo adduct into a δ-lactone. This also shows that both termini of the key adduct, the diol acetonide and vinyl moiety, can be elaborated selectively into an acid function leading to both aminohydroxymethyl acid and diacid derivatives.
Key words
threose imines - allyl/1-butene-3-yl addition - aminohydroxymethyl acid - solvent effect - N-(1-phenylethyl) auxiliary
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