Stereodivergent syntheses of anisomycin derivatives from D-tyrosine.
[structures: see text] Enantiomerically pure 2-alkyl-3-acetoxy-4-iodopyrrolidines with all groups cis, and all adjacent groups trans (10 and 17), important precursors for the synthesis of pyrrolidinediols, have been prepared from D-tyrosine through regio- and diastereoselective reduction of a vinyl ketone and subsequent iodoamidation controlled by minimization of nonbonding steric interactions. Highly stereodivergent Woodward-Prevost methodology, applied to both iodopyrrolidines, yielded enantiomerically pure (2R,3R,4R)-, (2R,3R,4S)-, and (2R,3S,4R)-deacetylanisomycin (3, 4, and 5), each in excellent de. Incorporation of differential protection of the hydroxyl groups led to a one-pot synthesis of (2R,3R,4R)-anisomycin 2.
Kim
Jin Hyo
JH
Department of Agricultural Chemistry, Division of Applied Life Science (BK21 programs), Gyeongsang National University, Jinju, 660-701, South Korea.
Curtis-Long
Marcus J
MJ
Seo
Woo Duck
WD
Ryu
Young Bae
YB
Yang
Min Suk
MS
Park
Ki Hun
KH
D000841:Anisomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014443:Tyrosine / Q000737:chemistry*
D014443:Tyrosine; D000841:Anisomycin