1310340-07-8Relevant academic research and scientific papers
Pd-Catalyzed Carbonylation of Vinyl Triflates to Afford α,β-Unsaturated Aldehydes, Esters, and Amides under Mild Conditions
Zhang, Shaoke,Neumann, Helfried,Beller, Matthias
supporting information, p. 3528 - 3532 (2019/05/24)
An efficient and general protocol for the synthesis of α,β-unsaturated aldehydes, esters, and amides via carbonylation of vinyl triflates including derivatives of camphor, ketoisophorone, verbenone, and pulegone was developed. Crucial for these transformations is the use of a specific palladium catalyst containing a pyridyl-substituted dtbpx-type ligand. This procedure also allows for an easy access of dicarbonylated products from the corresponding ketones.
Divergent total synthesis of the lycopodium alkaloids huperzine A, huperzine B, and huperzine U
Ding, Rui,Fu, Jian-Guo,Xu, Guang-Qiang,Sun, Bing-Feng,Lin, Guo-Qiang
, p. 240 - 250 (2014/01/17)
Huperzine A, huperzine B, and huperzine U are congeners isolated from the Chinese herb Huperzia serrata (=Lycopodium serratum) in minuscule amounts. The most efficient total synthesis of huperzine A, the first asymmetric total syntheses of huperzine B, and the first total synthesis of huperzine U have been achieved efficiently in overall yields of 17%, 10%, and 9%, respectively, each spanning 10-13 steps from (R)-pulegone. The featured steps include palladium-catalyzed Buchwald-Hartwig coupling and Heck cyclization reactions and an Ir-catalyzed olefin isomerization reaction. This work has established the absolute configurations of huperzine B and huperzine U and revealed that natural huperzine A, huperzine B, and huperzine U possess the same set of absolute stereochemistries, thus providing support for the potential role of huperzine B and huperzine U in the biosynthesis of huperzine A.
A new approach to the bicyclo[3.3.1]nonane framework of huperzine A-like molecules via palladium-catalyzed intramolecular γ-arylation
Ding, Rui,Lu, Yunyu,Yao, Hequan,Sun, Bingfeng,Lin, Guoqiang
scheme or table, p. 1097 - 1100 (2012/08/28)
In our synthetic studies toward huperzine A, a diastereoselective α′-alkylation of the α-amido-γ-methyl hexenone 4 was realized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and unprecedented palladium-catalyzed intramolecular γ-arylation of 3 was observed, which generated 18 with bicyclo[3.3.1]nonane framework in satisfactory yield.
An efficient total synthesis of (-)-huperzine A
Ding, Rui,Sun, Bing-Feng,Lin, Guo-Qiang
supporting information, p. 4446 - 4449 (2012/10/29)
The total synthesis of Lycopodium alkaloid (-)-huperzine A has been accomplished in 10 steps with 17% overall yield from commercially abundant (R)-pulegone. The synthetic route features an efficient synthesis of 4 via a Buchwald-Hartwig coupling reaction,
Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one
Tun, Maung Kyaw Moe,Herzon, Seth B.
, p. 9422 - 9425,4 (2012/12/12)
A three-step synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one (1) from (R)-(+)-pulegone (3), proceeding in 44% overall yield, is described. The sequence comprises vinyl triflate formation, site-selective ozonolysis, and reduction. The route requires only one chromatographic purification and provides a convenient method to access multigram quantities of (R)-(+)-4-methylcyclohex- 2-ene-1-one (1).
Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one
Tun, Maung Kyaw Moe,Herzon, Seth B.
, p. 9422 - 9425 (2013/01/15)
A three-step synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one (1) from (R)-(+)-pulegone (3), proceeding in 44% overall yield, is described. The sequence comprises vinyl triflate formation, site-selective ozonolysis, and reduction. The route requires only one chromatographic purification and provides a convenient method to access multigram quantities of (R)-(+)-4-methylcyclohex- 2-ene-1-one (1).
Replacement of the hydrophobic part of 9-cis-retinoic acid with cyclic terpenoid moiety results in RXR-selective agonistic activity
Okitsu, Takashi,Sato, Kana,Iwatsuka, Kinya,Sawada, Natsumi,Nakagawa, Kimie,Okano, Toshio,Yamada, Shoya,Kakuta, Hiroki,Wada, Akimori
experimental part, p. 2939 - 2949 (2011/06/21)
Retinoid X receptor (RXR) agonists are interesting candidates for the treatment of metabolic syndrome. 9-Cis-retinoic acid (9cRA: 1) is a natural RXR agonist, that also works as a retinoic acid receptor (RAR) agonist. This fact prompted us to study the st
