Studies towards the synthesis of epothilone A via organoboranes.
Studies towards the synthesis of epothilone A via organoboranes have been described. A modified procedure for the large-scale preparation of B-gamma,gamma-dimethylallyldiisopinocampheylborane from prenyl alcohol has been developed. This reagent, upon reaction with various aldehydes, provides the corresponding alpha,alpha-dimethylhomoallylic alcohols in high enantioselectivities. The application of this reagent for the synthesis of the C1-C6 subunit of epothilone has been demonstrated. Alternatively, inter- and intramolecular asymmetric reduction protocols have also been utilized for the synthesis of the C1-C6 subunit of epothilone A. The synthesis of the C7-C21 fragment of epothilone A involving asymmetric alkoxyallyl- and crotylboration using alpha-pinene-derived reagents has also been described.
Ramachandran
P Veeraraghavan
PV
Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, West Lafayette, IN 47907-2084, USA. chandran@purdue.edu
Chandra
J Subash
JS
Prabhudas
Bodhuri
B
Pratihar
Debarshi
D
Reddy
M Venkat Ram
MV
D001880:Boranes / Q000737:chemistry*; D034261:Epothilones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D001880:Boranes; D034261:Epothilones; C093787:epothilone A