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Synthesis 2009(16): 2778-2784
DOI: 10.1055/s-0029-1216898
DOI: 10.1055/s-0029-1216898
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Regioselective Tsuji-Trost Pentadienylation of 3-Allyltetronic Acid
Further Information
Received
16 March 2009
Publication Date:
14 July 2009 (online)
Publication History
Publication Date:
14 July 2009 (online)
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Abstract
A regioselective Tsuji-Trost reaction of sodium 3-allyl-tetronate with methyl 5-trimethylsilylpenta-2,4-dienyl carbonate was developed. Carbon-carbon bond formation at the more highly substituted terminus of the pentadienyl residue was possible by introduction of an easy to remove SiMe3 shielding group at the remote end of the π-system. This carbonate reacted fast enough to avoid scrambling and formation of symmetric bisallyl tetronic acids. The 3-allyl-3-penta-2,4-dienyltetronic acid thus obtained is a key intermediate en route to the natural spirolactone bakkenolide A.
Key words
allylation - regioselectivity - palladium - tetronic acid - Schlosser-Wittig reaction
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