TY - JOUR
T1 - Studies towards the synthesis of epothilone A via organoboranes
AU - Ramachandran, P. Veeraraghavan
AU - Chandra, J. Subash
AU - Prabhudas, Bodhuri
AU - Pratihar, Debarshi
AU - Reddy, M. Venkat Ram
PY - 2005/10/21
Y1 - 2005/10/21
N2 - Studies towards the synthesis of epothilone A via organoboranes have been described. A modified procedure for the large-scale preparation of B-γ,γ-dimethylallyldiisopinocampheylborane from prenyl alcohol has been developed. This reagent, upon reaction with various aldehydes, provides the corresponding α,α-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 C1-C2 fragment of epothilone A involving asymmetric alkoxyallyl- and crotylboration using α-pinene-derived reagents has also been described.
AB - Studies towards the synthesis of epothilone A via organoboranes have been described. A modified procedure for the large-scale preparation of B-γ,γ-dimethylallyldiisopinocampheylborane from prenyl alcohol has been developed. This reagent, upon reaction with various aldehydes, provides the corresponding α,α-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 C1-C2 fragment of epothilone A involving asymmetric alkoxyallyl- and crotylboration using α-pinene-derived reagents has also been described.
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U2 - 10.1039/b508001k
DO - 10.1039/b508001k
M3 - Article
C2 - 16211118
AN - SCOPUS:27744566399
SN - 1477-0520
VL - 3
SP - 3812
EP - 3824
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 20
ER -