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Synthesis 2000; 2000(9): 1305-1309
DOI: 10.1055/s-2000-6408
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A Short and Efficient Synthesis of 2R,3R,4R-3,4-Dihydroxyproline, 1,4-Dideoxy-1,4-imino-l-xylitol, 2R,3R,4R,5S-3,4,5-Trihydroxypipecolic Acid, and 1,5-Dideoxy-1,5-imino-l-iditol

Byong Won Lee* , Ill-Yun Jeong, Min Suk Yang, Sang Uk Choi, Ki Hun Park
  • *Department of Agricultural Chemistry, Gyeongsang National University, Chinju 660-701, Korea; Fax + 82(5 91)7 57 01 78; E-mail: khpark@gshp.gsnu.ac.kr
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Publication Date:
31 December 2000 (online)

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The syntheses of pyrrolidine alkaloids (-)-1 and (+)-3 were accomplished in 47% and 60% overall yield from 2-azido-2-deoxy-l-idonate 5, while piperidine alkaloids (-)-2 and (+)-4 were obtained in 51% and 53% overall yield from the same starting material. Key step includes iodine promoted one-pot cyclization, and selective deprotection of isopropylidene and 9-phenylfluoren-9-yl (Pf) group.

carbohydrates - iodine - amino acids - one-pot cyclization - azasugars - protecting group

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