TY - JOUR
T1 - Total synthesis of attenols A and B
AU - Araki, Keisuke
AU - Suenaga, Kiyotake
AU - Sengoku, Tetsuya
AU - Uemura, Daisuke
N1 - Funding Information:
This work was supported in part by Wako Pure Chemical Industries Ltd, by Banyu Pharmaceutical Co., Ltd, and by Grants-in-Aid (Nos. 11558079 and 12045235) for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan. We thank Dr T. Yamori (Screening Committee of New Anticancer Agents supported by a Grant-in Aid for Scientific Research on Priority Area ‘Cancer’ from the Ministry of Education, Science, Sports, and Culture, Japan) for help with screening the human cancer cell line panel.
PY - 2002/3/4
Y1 - 2002/3/4
N2 - The enantioselective synthesis of attenols A and B, cyclic polyethers of marine origin, was accomplished on a semigram scale by using diastereoselective hydroboration, coupling with lithium acetylide, Lindlar reduction and acid-catalyzed acetal formation. The configuration of the remaining undetermined spiro acetal carbon was unambiguously determined to be 11S using this ample supply of attenol A. The antitumor activities of synthetic attenol A were also examined.
AB - The enantioselective synthesis of attenols A and B, cyclic polyethers of marine origin, was accomplished on a semigram scale by using diastereoselective hydroboration, coupling with lithium acetylide, Lindlar reduction and acid-catalyzed acetal formation. The configuration of the remaining undetermined spiro acetal carbon was unambiguously determined to be 11S using this ample supply of attenol A. The antitumor activities of synthetic attenol A were also examined.
KW - Biological studies
KW - Diastereoselective hydroboration
KW - Enantioselective synthesis
KW - Semigram scale
KW - Stereochemistry of spiro acetal ring
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U2 - 10.1016/S0040-4020(02)00056-X
DO - 10.1016/S0040-4020(02)00056-X
M3 - Article
AN - SCOPUS:0037017722
SN - 0040-4020
VL - 58
SP - 1983
EP - 1995
JO - Tetrahedron
JF - Tetrahedron
IS - 10
ER -
