Stereoselective Synthesis of 3, 6-Disubstituted-3, 6-dihydropyridin-2-ones as Potential Diketopiperazine Mimetics Using Organocopper-Mediated a nti-SN2'Reactions …

…, Y Sasaki, S Oishi, H Ohno, H Tamamura…

Index: Tamamura, Hirokazu; Koh, Yasuhiro; Ueda, Satoshi; Sasaki, Yoshikazu; Yamasaki, Tomonori; Aoki, Manabu; Maeda, Kenji; Watai, Yoriko; Arikuni, Hisashi; Otaka, Akira; Mitsuya, Hiroaki; Fujii, Nobutaka Journal of Medicinal Chemistry, 2003 ,  vol. 46,  # 9  p. 1764 - 1768

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Citation Number: 30

Abstract

Organocopper-mediated anti-SN2'reactions of γ-phosphoryloxy-α, β-unsaturated-δ-lactams were used to prepare highly functionalized diketopiperazine mimetics. The substrate phosphates 24, 32, and 47 were prepared from α-amino acid-derived allylic alcohols 10 by a sequence of reactions that included ring-closing metathesis. In the reactions of phosphates with organocopper reagents, the addition of LiCl dramatically improved anti-SN2' ...