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Two different reactions were experimented for the construction of the eight-membered B-ring of taxane skeleton through the formation of the C9-C10 bond. A SmI 2 promoted radical reaction on seco-alkynyl aldehydes 11cis or 11trans failed. A Nozaki/Kishi reaction carried out on the seco-iodovinyl aldehyde 12trans led, through an unprecedented intramolecular S N 2 reaction, to the...
A highly diastereoselective synthesis of the taxane potential precursor 16 is achieved. An unexpected diastereoselectivity was observed upon condensation of the α-trimethylsilyloxyaldehydes 9a or 9b with the cyclohexenyllithium 10. The single diol isomers 13A and 14A exhibiting the required 1β,2α relative configuration are obtained in good yields.
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