90545-43-0Relevant articles and documents
Four-Step One-Pot Catalytic Asymmetric Synthesis of Polysubstituted Tricyclic Compounds: Lipase-Catalyzed Dynamic Kinetic Resolution Followed by an Intramolecular Diels-Alder Reaction
Tsuchimochi, Izuru,Hori, Shuhei,Takeuchi, Yasuo,Egi, Masahiro,Satoh, Tomo-O,Kanomata, Kyohei,Ikawa, Takashi,Akai, Shuji
, p. 822 - 828 (2021/02/16)
Starting from readily available tertiary alcohols, four different reactions (a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels-Alder reaction) took place under co-catalysis by lipase and oxovanadium compounds in a one-pot process to produce polysubstituted tricyclic carbon frameworks in high yields and with high enantioselectivities. The key to the success of this process was the discovery that a silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration.
A ring-closing enyne metathesis approach to functionalized semicyclic dienes: The total synthesis of (-)-tetrangomycin
Moodie, Lindon W. K.,Larsen, David S.
supporting information, p. 1684 - 1694 (2014/03/21)
The angucycline antibiotic (-)-tetrangomycin was synthesized in 13 steps (11 % overall yield) by using a stereoselective Diels-Alder reaction between a naphthoquinone and a semicyclic diene to construct the benz[a]anthraquinone ring system. The diene inte
From planning to optimization: Total synthesis of valerenic acid and some bioactive derivatives
Ramharter, Juergen,Mulzer, Johann
experimental part, p. 2041 - 2053 (2012/05/05)
A detailed study of the total synthesis of valerenic acid, a well known GABAA receptor subtype modulator, is described. Both successful as well as unsuccessful attempts towards the synthesis of the title compound are presented, including four different strategies to synthesize one of the key intermediates. The first two strategies are based on epoxides provided from the chiral pool, whereas the last two approaches rest on stereocontrolled modifications of 2-cyclopentenone. The streamlined synthesis implements a new one-pot reaction, which combines the addition of a Grignard species with an acid-catalyzed isomerization of the intermediate allylic alcohol. Further highlights are a stereo- and regioselective hydroxy-directed Diels-Alder reaction, a hydroxy-directed hydrogenation, and a final Negishi coupling reaction. After optimization of our synthesis, the preparation of several easily available derivatives is also discussed. Amides obtained by functionalization of the carboxyl group are more than twice as active as valerenic acid. The development and optimization of four different approaches towards valerenic acid (1) are described. The shortest approach spans 10 steps and provides valerenic acid in 25 % overall yield by incorporating a new one-pot reaction, an extremely stereo- and regioselective metal-coordinated Diels-Alder reaction, a hydroxy-directed hydrogenation, and a final Negishi coupling reaction. Copyright
