TY - JOUR
T1 - Absolute configuration of (+)-aureothin
T2 - A toxic metabolite possessing γ-pyrone unit
AU - Ishibashi, Y.
AU - Ohba, S.
AU - Nishiyama, S.
AU - Yamamura, S.
PY - 1995/12/1
Y1 - 1995/12/1
N2 - The absolute configuration of aureothin (1) has been determined by synthesis of (-)-aureonone (4) bearing R-configuration. X-Ray single crystallographic analysis of 21 guaranteed the stereochemistry of the chiral center introduced by Sharpless asymmetric epoxidation, as well as that of isoaureothin (3) which was previously synthesized in a similar pathway. Aureothin (1) itself was also synthesized, although Wittig coupling reaction of 4 under basic conditions, caused a partial epimerization of the chiral center.
AB - The absolute configuration of aureothin (1) has been determined by synthesis of (-)-aureonone (4) bearing R-configuration. X-Ray single crystallographic analysis of 21 guaranteed the stereochemistry of the chiral center introduced by Sharpless asymmetric epoxidation, as well as that of isoaureothin (3) which was previously synthesized in a similar pathway. Aureothin (1) itself was also synthesized, although Wittig coupling reaction of 4 under basic conditions, caused a partial epimerization of the chiral center.
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U2 - 10.1246/bcsj.68.3643
DO - 10.1246/bcsj.68.3643
M3 - Article
AN - SCOPUS:0029621182
SN - 0009-2673
VL - 68
SP - 3643
EP - 3649
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 12
ER -