Journal of Organic Chemistry p. 1166 - 1170 (1991)
Update date:2022-08-04
Topics:
Magnus, Philip
Thurston, Lee S.
(R)-(-)-Ethyl nipecotate 6 was converted into the N-allyl bromide 10 whose derived Grignard reagent 11 was added to N-(phenylsulfonyl)-2-(methoxyoxalyl)indole 12 to give the diastereomeric alcohols 13.Removal of the indole protecting group from 13 and coupling with vindoline gave the separable diastereomers 15(S) and 17(R).Deprotection of 15/17 and treatment with formaldehyde/acetic acid gave desethyldihydronavelbine 5, and its 18'-epimer 19.Only the natural 18'-epimer exhibited any antitumor activity.
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