150615-45-5Relevant 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.
Quasiracemic synthesis: Concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine
Zhang, Qisheng,Rivkin, Alexey,Curran, Dennis P.
, p. 5774 - 5781 (2007/10/03)
The concept of quasiracemic synthesis is introduced and illustrated with syntheses of both enantiomers of pyridovericin (whose absolute configuration is assigned as R) and mappicine. Like racemic synthesis, quasiracemic synthesis provides both enantiomers in a single synthetic sequence; however, separation tagging is used to ensure that quasiracemic mixtures can be analyzed, separated, and identified on demand. Fluorous tags of differing chain lengths are used to tag two enantiomeric starting materials. The resulting quasienantiomers are mixed to make a quasiracemate, which is then treated like a true racemate in successive steps of the synthesis. Fluorous chromatography is used to separate, or demix, the final quasiracemate into its two components, which are then detagged to provide (true) enantiomeric products. Quasiracemic synthesis is portrayed as the first and simplest of a series of mixture synthesis techniques based on separation tagging, and the prospects for using other types of separation tags are briefly evaluated.
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).
