TY - JOUR
T1 - Enantiospecific syntheses of valienamine and 2-epi-valienamine
AU - Shing, Tony K.M.
AU - Li, Tin Y.
AU - Kok, Stanton H.L.
PY - 1999/3/19
Y1 - 1999/3/19
N2 - Cyclic sulfite 10, readily available from (-)-quinic acid (3) in 10 steps, was ring opened regio- and stereospecifically with azide anion to give (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene- 2,3,4-triol (11). Deprotection of 11 afforded, for the first time, 2- epivalienamine (2), which was isolated as penta-N,O-acetyl-2-epi-valienamine (14). The configuration of the free hydroxy group in 11 was inverted by a two-step sequence to give the blocked valienamine 19 that was deprotected to give valienamine (1), isolated as penta-N,O-acetylvalienamine (21). This approach furnished (+)-valienamine (1) in 16 steps (7% overall yield) and recorded the first synthesis of 2-epi-valienamine (2) in 13 steps (11% overall yield).
AB - Cyclic sulfite 10, readily available from (-)-quinic acid (3) in 10 steps, was ring opened regio- and stereospecifically with azide anion to give (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene- 2,3,4-triol (11). Deprotection of 11 afforded, for the first time, 2- epivalienamine (2), which was isolated as penta-N,O-acetyl-2-epi-valienamine (14). The configuration of the free hydroxy group in 11 was inverted by a two-step sequence to give the blocked valienamine 19 that was deprotected to give valienamine (1), isolated as penta-N,O-acetylvalienamine (21). This approach furnished (+)-valienamine (1) in 16 steps (7% overall yield) and recorded the first synthesis of 2-epi-valienamine (2) in 13 steps (11% overall yield).
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U2 - 10.1021/jo982024i
DO - 10.1021/jo982024i
M3 - Article
AN - SCOPUS:0033583159
SN - 0022-3263
VL - 64
SP - 1941
EP - 1946
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 6
ER -