60241-78-3Relevant academic research and scientific papers
Hyperconjomer stereocontrol of cationic polyene cyclisations
Rodger, Robert T.,Graham, Marlowe S.,McErlean, Christopher S. P.
, p. 8551 - 8560 (2019)
Polyene cyclisations are a powerful method for the direct generation of molecular complexity. This paper describes the use of computational methods to investigate the stereoselectivity of cationic polyene cyclisations of geranylbenzene derivatives. The ou
Total Synthesis of (±)-Brussonol and (±)-Komaroviquinone via a Regioselective Cross-Electrophile Coupling of Aryl Bromides and Epoxides
Ahmad, Anees,Burtoloso, Antonio C. B.
supporting information, p. 6079 - 6083 (2019/08/26)
The short and stereoselective syntheses of diterpenes (±)-brussonol and (±)-komaroviquinone, via a Ni-catalyzed epoxide ring-opening approach in the presence of aryl halides, is described. Key steps involve the effective preparation of a challenging hemia
Total syntheses of (±)-taiwaniaquinol D and (±)-taiwaniaquinone D via a key Lewis acid-catalyzed Nazarov type cyclization
Kakde, Badrinath N.,Parida, Amarchand,Kumari, Pooja,Bisai, Alakesh
, p. 3179 - 3184 (2016/07/06)
Total syntheses of structurally intriguing taiwaniaquinoids viz (±)-taiwaniaquinol D (1e) and (±)-taiwaniaquinone D (1h) have been disclosed via a key Lewis acid catalyzed Nazarov type cyclization of arylvinylcarbinols.
Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A
Kakde, Badrinath N.,Kumar, Nivesh,Mondal, Pradip Kumar,Bisai, Alakesh
, p. 1752 - 1755 (2016/05/19)
A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)2 and Bi(OTf)3 in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).
Total Synthesis of (±)-Taiwaniaquinol F and Related Taiwaniaquinoids
Kakde, Badrinath N.,Kumari, Pooja,Bisai, Alakesh
, p. 9889 - 9899 (2015/11/03)
Total synthesis of (±)-taiwaniaquinol F (1a) has been accomplished via an efficient Lewis acid-catalyzed Nazarov-type cyclization of aryldiallylcarbinols (±)-2e derived from safranal 7. The methodology works under mild conditions using only 2 mol % of met
Synthesis of (±)- and (+)-perovskone
Majetich, George,Zhang, Yong,Tian, Xinrong,Britton, Jonathan E.,Li, Yang,Phillips, Ryan
experimental part, p. 10129 - 10146 (2012/02/03)
A biomimetic synthesis of the triterpene (±)-perovskone was achieved featuring a remarkable polycyclization process in which three rings, four bonds, and five stereocenters were created in a single operation in 82% yield. This convergent synthesis required 16 steps, starting from vanillin, and proceeded in 9% overall yield. A second route to prepare optically active quinone 2 took 15 steps in 36% overall yield and featured a palladium-catalyzed reductive allylic transposition to establish the C-5 chirality stereospecifically. Quinone (-)-2 was converted to (+)-perovskone (1) via a polycyclization cascade, which created four rings, five bonds, and six stereocenters in a single operation in 50% yield.
A formal total synthesis of salvadione
Maier, Martin E.,Bayer, Alexander
, p. 4034 - 4043 (2007/10/03)
The tricyclic 6-7-6 core structure of the triterpene salvadione (1) was obtained in an efficient manner from the aryl bromide 16 and the alkyl iodide 35 carrying a methylenecyclohexane group at the terminus. Alkylation of the anion derived from 16 with th
Stereoselective syntheses of (±)-komaroviquinone and (±)-faveline methyl ether through intramolecular Heck reaction
Sengupta, Sujaya,Drew, Michael G. B.,Mukhopadhyay, Ranjan,Achari, Basudeb,Banerjee, Asish Kr
, p. 7694 - 7700 (2007/10/03)
An efficient, flexible, and stereoselective convergent route for constructing the trans-10-hydroxy-1,1-dimethyloctahydrodibenzo[a,d]cyclohepten- 7-ones (5a-c) was achieved via intramolecular Heck reaction. This strategy has been successfully implemented for the syntheses of (±)-komaroviquinone (3) through (±)-coulterone dimethyl ether (5c) and (±)-faveline methyl ether (1a).
ortho-Directed metallation in the regiocontrolled synthesis of enantiopure 2- and/or 3-substituted (S)S (p-tolylsulfinyl)-1,4-benzoquinones
Carreno, M. Carmen,Garcia Ruano, Jose L.,Toledo, Miguel A.,Urbano, Antonio
, p. 913 - 921 (2007/10/03)
Enantiomerically pure (S)S-(p-tolylsulfinyl)-1,4-benzoquinones with alkyl and methoxy substituents at C-2 and/or C-3 are synthesized by CAN oxidation of adequately substituted (S)S-(p-tolylsulfinyl)-1,4-dimethoxyaromatic precursors 2 or 3. These compounds were obtained by ortho-directed metallation or bromo-metal exchange from the corresponding p-methoxyanisoles in a highly regiocontrolled manner.
Approach to the synthesis of candelabrone and synthesis of 3,7-diketo-12-hydroxyabieta-8,11,13-triene
Burnell, Robert H.,Caron, Stephane
, p. 1446 - 1454 (2007/10/02)
An approach to the synthesis of aromatic diterpenes was tested for its generality.Phenylacetonitriles with increasing substitution on the aromatic ring were prepared and alkylated with geranyl bromide and the resulting dienes subjected to cationic cycliza
