TY - JOUR
T1 - Total synthesis of elaiophylin (azalomycin B)
AU - Toshima, Kazunobu
AU - Tatsuta, Kuniaki
AU - Kinoshita, Mitsuhiro
N1 - Funding Information:
Acknowledgment: We are grateful to Prof. S. Umezawa, Institute of Bioorganic Chemistry, and Prof. H. Umezawa, Institute of Microbial Chemistry for their generous support of our program. Financial supports by the Ministry of Education, Science, and Culture (Grant-in-Aid for General Research) and by the Japan Antibiotics Research Association Research Grant are deeply acknowledged. We are indebted to Dr. H. Naganawa (Institute of Microbial Chemistry) for spectral analyses. We also thank Dr. M. Arai (Sankyo Co., Ltd.) for a generous gift of natural azalomycin B and its spectral data, and Messrs. K. Ishiyama and M. Horikoshi for their technical assistance.
PY - 1986
Y1 - 1986
N2 - Antibiotic elaiophylin 1a has been first synthesized by a convergent route involving aldol condensation between (5R,6R,7R)-5-0-[2′-deoxy-3′,4′-di-0-(dimethylisopropylsilyl)-α-L-fucopyranosyl]-6-ethyl-7-0-(diethylisopropylsilyl)-5,7-dihydroxy-3-octanone 3a and (7S,8S,15S, 16S) - (3E, 5E, 11E, 13E) -8,16-bis [ (1 ′R) -1′ -formylethyl] -7,15-dimethyl-1, 9-dioxacyclohexadeca-3,5, 11,13-tetraene-2,10-dione 4, followed by desilylation. The segments, 3a and 4, were synthesized from D-glucose and 2-deoxy-L-fucose.
AB - Antibiotic elaiophylin 1a has been first synthesized by a convergent route involving aldol condensation between (5R,6R,7R)-5-0-[2′-deoxy-3′,4′-di-0-(dimethylisopropylsilyl)-α-L-fucopyranosyl]-6-ethyl-7-0-(diethylisopropylsilyl)-5,7-dihydroxy-3-octanone 3a and (7S,8S,15S, 16S) - (3E, 5E, 11E, 13E) -8,16-bis [ (1 ′R) -1′ -formylethyl] -7,15-dimethyl-1, 9-dioxacyclohexadeca-3,5, 11,13-tetraene-2,10-dione 4, followed by desilylation. The segments, 3a and 4, were synthesized from D-glucose and 2-deoxy-L-fucose.
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U2 - 10.1016/S0040-4039(00)85053-4
DO - 10.1016/S0040-4039(00)85053-4
M3 - Article
AN - SCOPUS:0022470772
SN - 0040-4039
VL - 27
SP - 4741
EP - 4744
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 39
ER -