The Journal of Organic Chemistry

Asymmetric synthesis. 2. Practical method for the asymmetric synthesis of indolizidine alkaloids: total synthesis of (-)-monomorine I

J Royer, HP Husson

Index: Royer, Jacques; Husson, Henri-Philippe Journal of Organic Chemistry, 1985 , vol. 50, # 5 p. 670 - 673

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Citation Number: 83

Abstract

The alkylation of the chiral2-cyano-6-oxazolopipridine synthon (1) with the iodo ketal 2 gave, after selective cleavage of the cyano group, the oxazolopiperidine 4 having the 2s configuration. Compound 4 was alkylated with CH3MgI, giving a 4 1 mixture of alcohols 6 and 7 in which the major product 6 possessed the desired 2, 6-cis configuration. Treatment of 6 under acidic hydrogenation conditions (H2, Pd/C, H+) led to the desired (-)- ...