871809-93-7Relevant articles and documents
Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
Pandey, Ganesh,Laha, Ramkrishna,Mondal, Pradip Kumar
, p. 9689 - 9692 (2019/08/15)
A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.
Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid
Bochicchio,Schiavo,Chiummiento,Lupattelli,Funicello,Hanquet,Choppin,Colobert
, p. 8859 - 8869 (2018/11/30)
Myricanol 1, a constituent of Myrica species, has been reported to lower the levels of the microtubule-associated protein tau (MAPT), whose accumulation plays an important role in some neurodegenerative diseases, such as Alzheimer's disease (AD). Herein w
Lipase-catalyzed resolution of 1-[4-(benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-centrolobine
Tadiparthi, Krishnaji,Raghavendra,Kamal, Ahmed
, p. 2321 - 2326 (2017/10/06)
A practical and efficient method for the preparation of homoallylic alcohol and its successful enzymatic resolution has been developed. This lipase-catalyzed resolution process has been optimized with respect to different lipases and solvents. Moreover, M
The biomimetic synthesis and final structure determination of (+)- and (-)-centrolobine, naturally occurring diarylheptanoid 2,6-cis-disubstituted tetrahydro-2H-pyrans
Rogano, Frank,Rueedi, Peter
experimental part, p. 1281 - 1298 (2010/09/12)
The enantiomerically pure title compounds were prepared by oxidative cyclization of their optically active diarylheptanoid precursors. The approach is considered as a biomimetic phenol oxidation via an intermediate quinone methide. The absolute configuration of the precursors is retained, and the transition state adopts the sterically most favorable diequatorial arrangement of the 2,6-substituents to afford the cis-configured natural products. The outcome unambiguously establishes the absolute configurations and the correlation with the chiroptical data. In addition, a problem of regioisomerism that had not been discussed before was solved, and the original assignment of the position of the MeO group in the natural centrolobines could be confirmed. As such the results are the experimental evidence for the corrections of long-term inconsistencies we had postulated in an earlier review article.
Enantioselective synthesis and absolute configurations of aculeatins A, B, D, and 6-epi-aculeatin D
álvarez-Bercedo, Paula,Falomir, Eva,Carda, Miguel,Marco
, p. 9641 - 9649 (2007/10/03)
The three naturally occurring, bioactive spiroacetals aculeatins A, B, and D, as well as the non-natural 6-epi-aculeatin D have been synthesized for the first time in enantiopure form using an asymmetric allylation as the only chirality source. A further
Suppression of epimerization due to selectivity leakage: An application towards the total synthesis of (-)-centrolobine
Lee, Cheng-Hsia Angeline,Loh, Teck-Peng
, p. 1641 - 1644 (2007/10/03)
An InCl3-mediated Prins cyclization of homoallylic alcohols with aldehydes has been established. The enantioselectivities of the trisubstituted tetrahydropyrans are almost retained through the suppression of epimerization. The synthetic value o
Enantioselective synthesis and absolute configurations of aculeatins A and B
Falomir, Eva,álvarez-Bercedo, Paula,Carda, Miguel,Marco, J. Alberto
, p. 8407 - 8410 (2007/10/03)
The two naturally occuring, bioactive spiroacetals aculeatins A and B have been synthesized for the first time in enantiopure form using an asymmetric allylation as the only chirality source. A further key step was a stereoselective aldol reaction with re
Total synthesis of (-)-centrolobine: β-C-glycoside formation via a tandem Grignard addition and stereoselective hemi-ketal reduction
Jennings, Michael P.,Clemens, Ryan T.
, p. 2021 - 2024 (2007/10/03)
It has been demonstrated that an aryl-β-C-glycoside can be efficiently constructed via a sequence consisting of Brown asymmetric allylation, ring-closing metathesis, hydrogenation, nucleophilic addition, and stereoselective Et3SiH reduction. Th