152708-69-5Relevant academic research and scientific papers
Enantioselective total synthesis of cis-trikentrin B
Lee, Mase,Ikeda, Izumi,Kawabe, Tsuyoshi,Mori, Sayaka,Kanematsu, Ken
, p. 3406 - 3416 (2007/10/03)
Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.
Preparation of alkyl-substituted indoles in the benzene portion. Part 11. Total synthesis of (6R,8S)-herbindole A, (6R,8S)-herbindole B, (6R,8S)-herbindole C (6R,8S)-cis-trikentrin A, (6R,8S)-cis-trikentrin B, (6R,8R)-trans-trikentrin B, and (6R,8R)-iso-t
Muratake,Mikawa,Seino,Natsume
, p. 854 - 864 (2007/10/02)
The key intermediate, (3R,5S)-3,5-dimethyl-1-cyclopentenylmethanol (13) for chiral syntheses of herbindoles and trikentrins, was prepared from the known Diels-Alder adduct 12. Employing pertinent methodologies developed in the previous model study (preced
Total synthesis of (6R,8S)-cis-trikentrin B, (6R,8R)-trans-trikentrin B, and (6R,8R)-iso-trans-trikentrin B. determination of the absolute structures of the natural trikentrins B
Muratake, Hideaki,Seino, Takako,Natsume, Mitsutaka
, p. 4815 - 4818 (2007/10/02)
The absolute structures of cis-trikentrin B, trans-trikentrin B, and iso-trans-trikentrin B were established to be 1, 2, and 3 by synthesizing the titled trikentrins 1,18b and 25 in an enantiospecific manner from a chirality-defined Diels-Alder adduct 7.
