Tetrahedron

Conformationally constrained analogues of diacylglycerol (DAG). Part 19: Asymmetric syntheses of (3R)-and (3S)-3-hydroxy-4, 4-disubstituted heptono-1, 4-lactones …

K Nacro, J Lee, JJ Barchi, NE Lewin, PM Blumberg…

Index: Nacro, Kassoum; Lee, Jeewoo; Barchi Jr., Joseph J; Lewin, Nancy E; Blumberg, Peter M; Marquez, Victor E Tetrahedron, 2002 , vol. 58, # 26 p. 5335 - 5345

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Citation Number: 15

Abstract

The stereospecific introduction of (R)-and (S)-OH groups at position C-3 of two diacylglycerol γ-lactones (DAG-lactones) previously identified as strong protein kinase C (PK-C) ligands is presented. The compounds were designed to investigate whether the extra OH group in a specific orientation could establish an additional hydrogen bond with the C1 domain of PK-C, thus providing a DAG analogue with reduced lipophilicity. The OH ...