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.
[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.
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002614:Chelating Agents / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D011090:Polyenes; D020005:Propanols / Q000737:chemistry*; D011753:Pyrones; D013237:Stereoisomerism
D000475:Alkenes; D002614:Chelating Agents; D007659:Ketones; D011090:Polyenes; D020005:Propanols; D011753:Pyrones; C006463:allyl alcohol; C040313:fostriecin