TY - JOUR
T1 - Stereochemistry of theonezolides A-C
AU - Nozawa, Kohei
AU - Tsuda, Masashi
AU - Tanaka, Naonobu
AU - Kubota, Takaaki
AU - Fukushi, Eri
AU - Kawabata, Jun
AU - Kobayashi, Jun'Ichi
N1 - Funding Information:
We thank Ms. S. Oka, Center for Instrumental Analysis, Hokkaido University, for measurements of ESIMS. This work was partly supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan .
PY - 2013/2/20
Y1 - 2013/2/20
N2 - Theonezolides A-C (1-3) are cytotoxic 37-membered macrolides with a long side chain isolated from an Okinawan marine sponge Theonella sp. The relative stereochemistry of 1-3 was investigated by combination of NMR analysis including application of a JBCA method, a Universal NMR database, and a 13C-acetonide method. Furthermore, the absolute configurations at 14 chiral centers in 1-3 were found to be 19S, 22R, 24S, 28S, 44S, 45S, 47R, 49S, 53R, 55S, 57S, 59S, 60S, and 63S by application of a modified Mosher's method.
AB - Theonezolides A-C (1-3) are cytotoxic 37-membered macrolides with a long side chain isolated from an Okinawan marine sponge Theonella sp. The relative stereochemistry of 1-3 was investigated by combination of NMR analysis including application of a JBCA method, a Universal NMR database, and a 13C-acetonide method. Furthermore, the absolute configurations at 14 chiral centers in 1-3 were found to be 19S, 22R, 24S, 28S, 44S, 45S, 47R, 49S, 53R, 55S, 57S, 59S, 60S, and 63S by application of a modified Mosher's method.
KW - C-acetonide method
KW - JBCA method
KW - Stereochemistry
KW - Theonezolides A-C
KW - Universal NMR database
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U2 - 10.1016/j.tetlet.2012.11.120
DO - 10.1016/j.tetlet.2012.11.120
M3 - Article
AN - SCOPUS:84872286015
SN - 0040-4039
VL - 54
SP - 783
EP - 787
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 8
ER -
