808750-22-3Relevant academic research and scientific papers
Redox-Neutral Coupling between Two C(sp3)?H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles
Rocaboy, Ronan,Anastasiou, Ioannis,Baudoin, Olivier
supporting information, p. 14625 - 14628 (2019/09/16)
The intramolecular coupling of two C(sp3)?H bonds to forge a C(sp3)?C(sp3) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3)?C(sp3) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with the C?Br bond acting as an internal oxidant. Furthermore, it allows the coupling between two moderately acidic primary or secondary C?H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C?H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3)-C(sp3) bonds.
Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A
Liu, Feipeng,Dong, Zhe,Wang, Jianchun,Dong, Guangbin
supporting information, p. 2144 - 2148 (2019/01/24)
To show the synthetic utility of palladium/norbornene (Pd/NBE) cooperative catalysis, here we report concise syntheses of indenone-based natural products, pauciflorol F and acredinone A, which are enabled by direct annulation between aryl iodides and unsa
Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions
Chandrasekhar,Reddy, N. Ramakrishna,Rao, Y. Srinivasa
, p. 12098 - 12107 (2007/10/03)
A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C.
Towards a total synthesis of the new anticancer agent mensacarcin: Synthesis of the carbocyclic core
Tietze, Lutz F.,Stewart, Scott G.,Polomska, Marta E.,Modi, Andrea,Zeeck, Axel
, p. 5233 - 5242 (2007/10/03)
A synthesis of the carbocyclic core associated with the new anti-cancer agent mensacarcin (1) is reported. The strategy involves the synthesis of several novel highly substituted aromatic compounds, such as 12 and 23. The lithium derivative of 12 readily
