157952-85-7Relevant academic research and scientific papers
Enantioselective synthesis of the tricyclic core of (+)-strigol
Takahashi, Aiko,Ogura, Yusuke,Enomoto, Masaru,Kuwahara, Shigefumi
, p. 6634 - 6639 (2016)
An enantioselective synthesis of the tricyclic core structure of (+)-strigol, a potent seed germination stimulant for root parasitic weeds, has been achieved from 2-iodo-4,4-dimethyl-2-cyclohexen-1-one in 14 steps. The key steps include a CBS reduction of an iodo enone to obtain a cyclohexenol derivative of high enantiomeric excess, regioselective epoxide ring opening with a Grignard reagent in a low-polarity solvent, highly diastereoselective addition of vinyllithium to a ketone, and Lewis acid-promoted installation an acetate unit onto a bicyclic allylic acetate intermediate.
Enantioselective Total Synthesis of Macfarlandin C, a Spongian Diterpenoid Harboring a Concave-Substituted cis-Dioxabicyclo[3.3.0]octanone Fragment
Allred, Tyler K.,Dieskau, André P.,Lackner, Gregory L.,Overman, Larry E.,Zhao, Peng
, p. 6268 - 6272 (2020)
The enantioselective total synthesis of the rearranged spongian diterpenoid (?)-macfarlandin C is reported. This is the first synthesis of a rearranged spongian diterpenoid in which the bulky hydrocarbon fragment is joined via a quaternary carbon to the h
General Access to Concave-Substituted cis-Dioxabicyclo[3.3.0]octanones: Enantioselective Total Syntheses of Macfarlandin C and Dendrillolide A
Allred, Tyler K.,Dieskau, André P.,Zhao, Peng,Lackner, Gregory L.,Overman, Larry E.
, p. 15532 - 15551 (2020/11/30)
The evolution of a strategy to access the family of rearranged spongian diterpenoids harboring a concave-substituted cis-2,8-dioxabicyclo[3.3.0]octan-3-one fragment is described. The approach involves late-stage fragment coupling of a tertiary-carbon radical and an electron-deficient double bond to form vicinal quaternary and tertiary stereocenters with high fidelity. A stereoselective Mukaiyama hydration is the key step in the subsequent elaboration of the cis-2,8-dioxabicyclo[3.3.0]octan-3-one moiety. This strategy was utilized in enantioselective total syntheses of (-)-macfarlandin C and (+)-dendrillolide A. An efficient construction of enantiopure tetramethyloctahydronaphthalenes was developed during the construction of (-)-macfarlandin C.
Catalytic asymmetric total syntheses of sesquiterpenoids, (+)- and (?)-ar-macrocarpene
Bisai, Vishnumaya,Khatua, Arindam,Roy, Avishek
supporting information, (2020/01/11)
Concise catalytic asymmetric total syntheses of aromatic sesquiterpenes, naturally occurring (+)-ar-macrocarpene (1) and unnatural (?)-ar-macrocarpene (ent-1) have been featured (6 steps, ～60–61% overall yields) from commercially available 4,4-dimethylcyc
Pd-catalyzed regioselective C?H alkenylation and alkynylation of allylic alcohols with the assistance of a bidentate phenanthroline auxiliary
Hirano, Koji,Miura, Masahiro,Xu, Shibo
supporting information, p. 9059 - 9064 (2020/12/02)
A Pd-catalyzed regioselective C?H alkenylation of allylic alcohols with electron-deficient alkenes has been developed. The key to success is the introduction of bidentately coordinating phenanthroline directing group, which enables the otherwise challenging and regioselective C?H activation at the proximal alkenyl C?H bonds over the conceivably competitive allylic C?O bond activation. The same Pd/phenanthroline system is efficient for the C?H alkynylation of allylic alcohols with alkynyl bromides.
Reductive Cyclization of o-Nitroarylated-α,β-unsaturated Aldehydes and Ketones with TiCl3/HCl or Fe/HCl Leading to 1,2,3,9-Tetrahydro-4 H-carbazol-4-ones and Related Heterocycles
Qiu, Yun,Dlugosch, Michael,Liu, Xin,Khan, Faiyaz,Ward, Jas S.,Lan, Ping,Banwell, Martin G.
, p. 12023 - 12033 (2018/10/02)
Compounds such as 3, the product of a palladium[0]-catalyzed Ullmann cross-coupling of o-iodonitrobenzene and 2-iodocyclohex-2-en-1-one, undergo complementary modes of reductive cyclization depending upon the conditions employed. Thus, on treatment with hydrogen in the presence of palladium on carbon, the tetrahydrocarbazole 4 is formed, while reaction of the same substrate (3) with TiCl3 in acetone affords the 1,2,3,9-tetrahydro-4H-carbazol-4-one 6.
Bis-Michael Acceptors as Novel Probes to Study the Keap1/Nrf2/ARE Pathway
Deny, Ludovic J.,Traboulsi, Hussein,Cantin, André M.,Marsault, éric,Richter, Martin V.,Bélanger, Guillaume
, p. 9431 - 9442 (2016/11/11)
Nuclear factor erythroid 2-related factor 2 (Nrf2) is a master regulator that promotes the transcription of cytoprotective genes in response to oxidative/electrophilic stress. Various Michael-type compounds were designed and synthesized, and their potency
Pd(PPh3)4/AgOAc-catalyzed one-pot synthesis of substituted 3,4-dihydronaphthalen-1(2H)-ones
Liu, Hui,Yan, Peiyun,Li, Yan,Liu, Jinliang,Sun, Qian,Wang, Xingbin,Wang, Cunde
scheme or table, p. 1055 - 1059 (2012/10/08)
A novel and efficient one-pot synthesis of 3,4-dihydronaphthalen-1(2/7)- ones by employing 2-iodocyclo-hex-2-enones, 1-alkynes, and a Pd[(C 6H5)3P]4/AgOAc catalytic system is described. The attractive features o
Highly enantioselective and regioselective carbonyl reduction of cyclic α,β-unsaturated ketones using TarB-N02 and sodium borohydride
Kim, Jinsoo,Bruning, John,Park, Kevin E.,Lee, David J.,Singaram, Bakthan
supporting information; experimental part, p. 4358 - 4361 (2009/12/24)
Asymmetric 1,2-reduction of α,β-unsaturated ketones using TarB-NO2 and NaBH4 Is reported. Simple cycloalkenones give products In low enantiomeric excess. However, cycloalkenones with a-substituents, such as halides, alkyl, and aryl, have been enantioselectively reduced with this system to yield chiral allylic alcohols In enantiomeric excess up to 99%. The starting materials for TarB-N02 are inexpensive, and the boronlc acid can be easily recovered In high yield by a simple acid extraction.
Suzuki cross-coupling/reductive debenzyloxycarbonylation sequence for the syntheses of [c]annulated isoquinolines: Application for the syntheses of pancratistatin-like isoquinolines
Pandey, Ganesh,Balakrishnan, Madhesan
, p. 8128 - 8131 (2008/12/22)
(Chemical Equation Presented) A two-step strategy involving Suzuki cross-coupling of boronic acids with a diverse array of α-iodoenones followed by hydrogenation is developed for the construction of [c]annulated isoquinolines. This mild and efficient proc
