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

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. Thi...

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Bibliographic Details
Published inOrganic letters Vol. 5; no. 20; pp. 3755 - 3757
Main Authors Ramachandran, PV, Liu, HP, Reddy, MVR, Brown, HC
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 02.10.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENTS
OLEFIN METATHESIS
ASYMMETRIC TOTAL-SYNTHESIS
PD 113,270
TUMOR AGENTS CI-920
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol035516c