220691-84-9Relevant academic research and scientific papers
Concise synthesis of the C15-C38 fragment of okadaic acid: Application of the Suzuki-Miyaura reaction to spiroacetal synthesis
Fuwa, Haruhiko,Sakamoto, Keita,Muto, Takashi,Sasaki, Makoto
, p. 366 - 369 (2015)
A concise synthetic entry to the C15-C38 fragment of okadaic acid by exploiting a Suzuki-Miyaura reaction for the rapid assembly of the spiroacetal substructures has been developed. The present synthesis was completed in 19 linear steps from a commercially available material, showcasing the efficiency of our synthetic strategy.
Concise synthesis of the C15-C38 fragment of okadaic acid, a specific inhibitor of protein phosphatases 1 and 2A
Fuwa, Haruhiko,Sakamoto, Keita,Muto, Takashi,Sasaki, Makoto
, p. 6369 - 6383 (2015/08/18)
Abstract A marine polyether natural product okadaic acid is known to be a potent and specific inhibitor of protein phosphatases 1 and 2A. Herein, concise synthesis of the C15-C38 fragment of okadaic acid is reported. We investigated two different strategies for the construction of two spiroacetal substructures found in the target compound. The first strategy involved Suzuki-Miyaura coupling for the synthesis of endocyclic enol ethers and subsequent spiroacetalization. The second strategy exploited Suzuki-Miyaura coupling for the synthesis of exo-olefins as the precursor of spiroacetals. An alkynylaluminum-anomeric sulfone coupling effectively assembled the key spiroacetal substructures and completed the target compound.
Total synthesis of the protein phosphatase inhibitor okadaic acid
Ley, Steven V.,Humphries, Alexander C.,Eick, Holger,Downham, Robert,Ross, Andrew R.,Boyce, Richard J.,Pavey, John B. J.,Pietruszka, Joerg
, p. 3907 - 3911 (2007/10/03)
The total synthesis of the protein phosphatase inhibitor okadaic acid 1 is reported using a convergent coupling strategy of three components, all of which may be prepared using chemistry developed in our laboratories.
