115352-45-9Relevant academic research and scientific papers
Synthesis of a marine polyether toxin, okadaic acid [1]1 1 Full Paper corresponding to the communications, M. Isobe, Y. Ichikawa and T. Goto, Tetrahedron Lett., 26, 5199 (1985); M. Isobe, Y. Ichikawa, D-L. Bai and T. Goto, Tetrahedron Lett., 26, 5203 (1985). - strategy and synthesis of segment a
Ichikawa, Yoshiyasu,Isobe, Minoru,Bai, Dong-Lu,Goto, Toshio
, p. 4737 - 4748 (2007/10/02)
The title compound was divided into three retrosynthetic segments A, B and C, by disconnecting two C-C bonds at C- 14 15 and C- 27 28. Segment A for okadaic acid synthesis comprises the carbon skeleton from C-1 through C-14, which was further disconnected at the bonds between C-8 and C-9 into two fragments A1 and A2. Each fragment was synthesized in the optically active form from D-glucose derivatives. Key steps are the oxymercuration and anti-selective heteroconjugate addition to elaborate the asymmetric carbons on acyclic parts of these fragments. The coupling was facilitated between the acetylenic carbanion and the lactone carbonyl of the respective fragments. The segment A was synthesized in 36 steps.
Synthetic studies toward marine toxic polyethers. 3. Stereocontrol for segment-A1 of okadaic acid by means of oxymercuration and epoxydation
Isobe,Ichikawa,Goto
, p. 5199 - 5202 (2007/10/02)
Segment-A1 of okadaic acid was synthesized from glucose via an acyclic stereocontrol for C-2 by means of oxymercuration. The stereochemistry was proven by comparison with S and R epoxides which were synthesized selectively by chelational and st
