Abstract
The palladium catalyzed carbonylation of 1 using the chiral ligand L1 afforded 2 in a highly diastereoselective manner. The stereochemistry of the major diastereomer 2a was determined by X-ray crystallographic analysis. AR luciferase reporter assay studies suggested that 2a was the active constituent of YK11 (2).
Highlights
Selective androgen receptor modulators (SARMs) are a class of androgen receptor (AR) ligands that show tissue-selective activation of androgenic signaling [1]
Major gray spheres; O, we performed an ARE-luciferase reporter assay in HEK293 cells to compare the partial agonistic of major diastereomer and the
The structure of the major diastereomer 2a was determined by X-ray crystallographic analysis
Summary
Selective androgen receptor modulators (SARMs) are a class of androgen receptor (AR) ligands that show tissue-selective activation of androgenic signaling [1]. YK11 is a mixture of two diastereomers (5:1), and the stereochemistry of the orthoester moiety positioned at the D-ring has not been determined yet. We reported the synthesis of 2 and related steroids having spiro-orthoester structures [3,5]. PdCl2 (CH3 CN) catalyzed carbonylation of 1 in the presence of p-benzoquinone in methanol afforded 2 as a 5:1 mixture of diastereomers in 43% yield (Scheme 1). We reported the asymmetric cyclization carbonylation of propargyl acetate using a Pd(tfa)2 /sulfoxide-oxazoline (sox) catalyst, which improved the yield and enantioselectivity [6]. On the basis of these recent findings, we report here the improved synthesis of 2 and elucidation of the stereochemistry of the biologically active diastereomer of 2. 43% yield synthesis of of YK11 as as a 5:1 mixture of
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