Determination of the absolute configuration of (+)-xestoaminol C [(2S, 3R)-2-amino-3-tetradecanol], a metabolite of Fiji sponge, Xestospongia sp., by the synthesis of its N,O-diacetyl derivative.
The N,O-diacetyl derivative of (+)-xestoaminol C (2-amino-3-tetradecanol, 1), an inhibitor of reverse transcriptase isolated from Xestospongia sp., was synthesized from (S)-alanine, and its absolute configuration was determined as 2S, 3R.
Ichihashi
Miwako
M
Department of Chemistry, Graduate School of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan.
Mori
Kenji
K
D000107:Acetylation; D000409:Alanine / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry*; D000818:Animals; D005233:Fatty Alcohols / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
D000605:Amino Alcohols; D005233:Fatty Alcohols; C476391:xestoaminol C; D000409:Alanine