Studies towards the synthesis of epothilone A via organoboranes.
Org Biomol Chem
; 3(20): 3812-24, 2005 Oct 21.
Article
in En
| MEDLINE
| ID: mdl-16211118
ABSTRACT
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.
Search on Google
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Boranes
/
Epothilones
Language:
En
Journal:
Org Biomol Chem
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2005
Document type:
Article
Affiliation country: