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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
Author(s) -
Show Krishanu,
Kumar Pradeep
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600625
Subject(s) - chemistry , hexane , aldol reaction , stereoselectivity , acetone , acetonide , stereochemistry , enantioselective synthesis , organocatalysis , chirality (physics) , catalysis , organic chemistry , medicine , surgery , triamcinolone acetonide , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
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 intermediates 11 were prepared with complete stereocontrol through the proline‐catalyzed intermolecular aldol reaction between acetone and d ‐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.