Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9‐epi‐Stagonolide C Employing Chiral Hexane‐1, 2, 3, 5‐tetraol Derivatives as Building Blocks. Issue 27 (26th August 2016)

• Record Type: Journal Article
• Authors: Show, Krishanu; Kumar, Pradeep
• Is Part Of: European journal of organic chemistry. Issue 27(2016)
• Page Start: 4696
• Page End: 4710
• Publication Date: 2016-08-26
• Subjects: Asymmetric synthesis -- Aldol reactions -- Metathesis -- α‐Aminoxylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600625
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An organocatalytic approach to the synthesis of (2 R, 3 S )‐hexane‐1, 2, 3, 5‐tetraol (11 ) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates11 were prepared with complete stereocontrol through the proline‐catalyzed intermolecular aldol reaction between acetone andd ‐glyceraldehyde acetonide. The synthetic utility of the intermediates was demonstrated by their transformation into the title hydroxylated pyrans and a variety of unsaturated lactones through standard synthetic protocols. Abstract : An organocatalytic approach to the synthesis of (2 R, 3 S )‐hexane‐1, 2, 3, 5‐tetraol derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The synthetic utility of the intermediates was demonstrated by their transformation into hydroxylated pyrans and a variety of unsaturated lactones through standard synthetic protocols.