A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-γ-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene.
Enantioselective synthesis of both enantiomers of gamma-ionone, gamma-damascone, karahana lactone and karahana ether / Stephen Beszant, Elios Giannini, Giuseppe Zanoni, Giovanni Vidari. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 13:12(2002 Jul 05), pp. 1245-1255. [10.1016/S0957-4166(02)00335-X]
Enantioselective synthesis of both enantiomers of gamma-ionone, gamma-damascone, karahana lactone and karahana ether
Elios Giannini;
2002
Abstract
A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-γ-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclization of methyl (6S)- or (6R)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate, respectively. The chiral information was encoded by a highly regioselective Sharpless asymmetric dihydroxylation of the corresponding diene.
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