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KMID : 1059519970410030150
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Journal of the Korean Chemical Society
1997 Volume.41 No. 3 p.150 ~ p.156
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Synthesis of a Precursor of Bulgecinine, (4S,5R)-1-Acetyl-2-formyl-5-benzyloxymethyl-4-pyrrolidinol
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Jeon Hak-Rim
Yoon Shin-Sook
Shin Young-Sook
Nam Jeong-E
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Abstract
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A precursor of bulgecinine, (4S,5R)-1-acetyl-2-formyl-5-benzyloxymethyl-4-pyrrolidinol (15) has been synthesized from diacetone-D-glucose. Barton deoxygenation, conversion to an L-sugar and displacement with N3- at C-5, and one-pot reductive cyclization at C-2 produced (6R)-6-Ο-benzyloxymethyl-(3R)-3-methoxy-2-oxa-5-azabicyclo-[2,2,1]heptane (13), a key intermediate for bulgecinine. N-Acetylation and acid hydrolysis of 13 furnished a precursor of bulgecinine, (2S,4S,5R)-pyrrolidinol derivative 15 and its (2R,4S,5R)-diastereomer.
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KEYWORD
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