Synthesis of homoallylic chiral tertiary alcohols via chelation-controlled diastereoselective nucleophilic addition on alpha-alkoxyketones: application for the synthesis of the C(1)-C(11) subunit of 8-epi-fostriecin |
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| Authors: | Ramachandran P Veeraraghavan Liu Haipeng Ram Reddy M Venkat Brown Herbert C |
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| Affiliation: | Herbert C. Brown Center for Borane Research, 560 Oval Drive, Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu |
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| Abstract: | [reaction: see text] Chiral beta-syn-alkoxyhomoallylic alcohols derived from alkoxyallylboration of aldehydes upon oxidation provided the corresponding chiral ketones. Chelation-controlled nucleophilic addition to these ketones occurred in a highly stereoselective manner to afford anti-homoallylic tertiary alcohols. This methodology has been applied for the synthesis of the C(1)-C(11) subunit of C(8)-epi-fostriecin. |
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