A Carbohydrate-Based Synthesis of the C13-C22 Fragment of Amphidinolide X

A facile carbohydrate‐based route was developed for the synthesis of the tetrahydrofuran (C13–C22) fragment of amphidinolide X. Starting from L‐sorbose, the key reactions followed include the stereoselective synthesis of a quaternary center at C1, Barton–McCombie deoxygenation at C2, Mitsunobu inver...

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Veröffentlicht in:European Journal of Organic Chemistry 2012-03, Vol.2012 (9), p.1753-1758
Hauptverfasser: Gurjar, Mukund K., Yellol, Gorakh S., Mohapatra, Debendra K.
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Sprache:eng
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Zusammenfassung:A facile carbohydrate‐based route was developed for the synthesis of the tetrahydrofuran (C13–C22) fragment of amphidinolide X. Starting from L‐sorbose, the key reactions followed include the stereoselective synthesis of a quaternary center at C1, Barton–McCombie deoxygenation at C2, Mitsunobu inversion at C3, and chain elongation by a Wittig reaction at C5. Synthesis of the C13–C22 fragment of amphidinolide X was achieved followingstereoselective installation of a quaternary center at C1, Barton–McCombie deoxygenation at C2, Mitsunobu inversion at C3, and chain elongation by a Wittig reaction at C5 as key reactions starting from L‐sorbose.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201101605