TY - JOUR
T1 - Two efficient four-step routes to marine toxin tanikolide
AU - Chen, Qingshou
AU - Deng, Haibing
AU - Zhao, Jingrui
AU - Lu, Yong
AU - He, Mingyuan
AU - Zhai, Hongbin
PY - 2005/8/29
Y1 - 2005/8/29
N2 - We have presented two facile four-step syntheses of (±)-tanikolide from ethyl 2-oxocyclopentanecarboxylate. The overall chemical yields of the two sequences reached as high as 76 and 85%, respectively. The first strategy involved alkylation, Baeyer-Villiger reaction, saponification, and reduction/lactonization. The second approach for synthesizing tanikolide took advantage of the same intermediate, the alkylated ketoester 2, which was converted to the target molecule in such three steps as deethoxycarbonylation, hydroxymethylation, and Baeyer-Villiger reaction. Our strategies are advantageous because of their high yields and suitability for the preparation of 1 in multigram or larger quantities.
AB - We have presented two facile four-step syntheses of (±)-tanikolide from ethyl 2-oxocyclopentanecarboxylate. The overall chemical yields of the two sequences reached as high as 76 and 85%, respectively. The first strategy involved alkylation, Baeyer-Villiger reaction, saponification, and reduction/lactonization. The second approach for synthesizing tanikolide took advantage of the same intermediate, the alkylated ketoester 2, which was converted to the target molecule in such three steps as deethoxycarbonylation, hydroxymethylation, and Baeyer-Villiger reaction. Our strategies are advantageous because of their high yields and suitability for the preparation of 1 in multigram or larger quantities.
KW - Marine natural product
KW - Syntheses
KW - Tanikolide
UR - https://www.scopus.com/pages/publications/23044439569
U2 - 10.1016/j.tet.2005.06.098
DO - 10.1016/j.tet.2005.06.098
M3 - 文章
AN - SCOPUS:23044439569
SN - 0040-4020
VL - 61
SP - 8390
EP - 8393
JO - Tetrahedron
JF - Tetrahedron
IS - 35
ER -
