157405-12-4Relevant academic research and scientific papers
Total synthesis of (+)-spiculoic acid A
Matsumura, Daisuke,Toda, Takumi,Hayamizu, Takashi,Sawamura, Kiyoto,Takao, Ken-ichi,Tadano, Kin-ichi
supporting information; experimental part, p. 3356 - 3358 (2009/09/05)
The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereoselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton.
Synthesis of six-membered compounds by environmentally friendly cyclization using indirect electrolysis
Ihara, Masataka,Katsumata, Akira,Setsu, Fumihito,Tokunaga, Yuji,Fukumoto, Keiichiro
, p. 677 - 684 (2007/10/03)
[Ni(cyclam)](ClO4)2-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.
Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization
Ihara, Masataka,Setsu, Fumihito,Shohda, Miyuki,Taniguchi, Nobuaki,Tokunaga, Yuji,Fukumoto, Keiichiro
, p. 5317 - 5323 (2007/10/02)
The radical cyclozations of (+/-)-(E)-3-((2-bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3--N-carbamoyl>prop-2-enoate (25) were carried out with (TMS)3SiH or Bu3SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25.The radical cyclization of (+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).
