Tetrahedron

Application of the β-azidonation reaction to the synthesis of the antitumor alkaloid (+)-pancratistatin

P Magnus, IK Sebhat

Index: Magnus, Philip; Sebhat, Iyassu K. Tetrahedron, 1998 , vol. 54, # 51 p. 15509 - 15524

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Citation Number: 72

Abstract

o-Vanillin21 was converted into24 following literature procedures. Treatment of24 withn- BuLi/THF followed by addition of25 gave26. Dehydration (POCl3/pyridine/DBU), hydrogenation and hydrolysis of26 gave the ketone29. Chirality was introduced by deprotonation of29 with the lithium salt of (+)-bis (α-methylbenzyl) amine, followed by triisopropylsilyl trifluoromethanesulfonate to give30 (95%). β-Azidonation of30 with (PhIO) ...