1448230-75-8Relevant academic research and scientific papers
Total synthesis and structure revision of didemnaketalB
Fuwa, Haruhiko,Muto, Takashi,Sekine, Kumiko,Sasaki, Makoto
, p. 1849 - 1860 (2014/03/21)
DidemnaketalB, a structurally complex spiroacetal that exhibits potent HIV-1 protease inhibitory activity, was originally discovered by Faulkner and his colleagues from the ascidian Didemnum sp. collected at Palau. Its absolute configuration was proposed
Total synthesis of the proposed structure of didemnaketal B
Fuwa, Haruhiko,Sekine, Kumiko,Sasaki, Makoto
, p. 3970 - 3973 (2013/09/02)
Total synthesis of the proposed structure of didemnaketal B has been accomplished. The C7-C21 spiroacetal domain was synthesized by exploiting our Suzuki-Miyaura coupling/spiroacetalization strategy. The C1-C7 acyclic domain was constructed via an Evans syn-aldol reaction and a vinylogous Mukaiyama aldol reaction. Finally, the C22-C28 side chain was introduced by means of a Nozaki-Hiyama-Kishi reaction. Comparison of the NMR spectroscopic data of our synthetic material with those of the authentic sample revealed that the proposed structure requires stereochemical reassignment.
