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

• Published in: European Journal of Organic Chemistry Vol. 2012; no. 9; pp. 1753 - 1758
• Main Authors: Gurjar, Mukund K., Yellol, Gorakh S., Mohapatra, Debendra K.
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.03.2012; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Cytotoxicity; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Macrolides; Mitsunobu inversion; Natural products; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Wittig reactions; PRACTICAL SYNTHESIS; Mitsunobu inversion; Wittig reactions; Natural products; Macrolides; Cytotoxicity; STEREOSELECTIVE-SYNTHESIS; MACRODIOLIDE; BOND; METATHESIS; DOUBLE INTRAMOLECULAR OXYMERCURATION; Wittig reaction; Barton-McCombie deoxygenation; Furan derivatives; Mitsunobu reaction; Chain elongation; Oside; Natural compound; Oxygen heterocycle; Macrolide; Tetrahydrofurane; Stereoselectivity; Sorbose; Chemical synthesis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201101605

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.