TY - JOUR
T1 - Long-range carbon-proton coupling constants for stereochemical assignment of acyclic structures in natural products
T2 - Configuration of the C5-C9 portion of maitotoxin
AU - Matsumori, Nobuaki
AU - Nonomura, Taro
AU - Sasaki, Makoto
AU - Murata, Michio
AU - Tachibana, Kazuo
AU - Satake, Masayuki
AU - Yasumoto, Takeshi
N1 - Funding Information:
Acknowledgments: We are grateful to Mr. S. Ishida of Yasumoto's laboratory for his assistance in purification of the sample; and to Messrs. T. Hinomoto, and Y. Kumaki, JEOL, for their technical help in determining HETLOC. The present study was supported in part by a Grant-in-Aid from the Ministry of Education, Science and Culture, Japan.
PY - 1996/2/19
Y1 - 1996/2/19
N2 - Long-range carbon-proton coupling constants (2,3J(C,H)) were measured for maitotoxin (MTX), one of the largest natural non-biopolymers, by hetero-half filter experiments and phase-sensitive HMBC with use of 9 mg of a 4% 13C-enriched sample. The necessary coupling constants within the terminal acyclic portions of MTX, where NOE analysis was not successful owing to the presumed coexistence of multiple conformers, were thus obtained for the resultant elucidation of relative configurations for the acyclic stereogenic centers to the 5R*, 7R*, 8R*, and 9S*.
AB - Long-range carbon-proton coupling constants (2,3J(C,H)) were measured for maitotoxin (MTX), one of the largest natural non-biopolymers, by hetero-half filter experiments and phase-sensitive HMBC with use of 9 mg of a 4% 13C-enriched sample. The necessary coupling constants within the terminal acyclic portions of MTX, where NOE analysis was not successful owing to the presumed coexistence of multiple conformers, were thus obtained for the resultant elucidation of relative configurations for the acyclic stereogenic centers to the 5R*, 7R*, 8R*, and 9S*.
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U2 - 10.1016/0040-4039(95)02413-1
DO - 10.1016/0040-4039(95)02413-1
M3 - Article
AN - SCOPUS:0030047690
SN - 0040-4039
VL - 37
SP - 1269
EP - 1272
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 8
ER -