56859-93-9Relevant academic research and scientific papers
Oxidative cyclizations: The asymmetric synthesis of (-)-alliacol A
Mihelcic, John,Moeller, Kevin D.
, p. 9106 - 9111 (2004)
A tandem anodic coupling-Friedel-Crafts alkylation strategy has been used to rapidly complete the asymmetric synthesis of alliacol A. The anodic oxidation reaction allowed for the generation of a new bond between two nucleophiles. In the synthesis, the ab
Asymmetric hydroformylation of vinylfurans catalyzed by {(11bS)-4-{[(1R)-2′-phosphino[1,1′-binaphthalen]-2-yl]oxy} dinaphtho[2,1-d:1′,2′-f]-[1,3,2]dioxaphosphepin}rhodium(I) [Rh I{(R,S)-binaphos}] derivatives
Nakano, Koji,Tanaka, Ryo,Nozaki, Kyoko
, p. 1681 - 1686 (2006)
The asymmetric hydroformylation of 2- and 3-vinylfurans (2a and 2b, resp.) was investigated by using [Rb{(R,S)-binaphos}] complexes as catalysts ((R,S)-binaphos=(11bS)-4-{[1R)-2′-phosphino[1,1′-binaphthalen]-2-yl] oxy}dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin; 1). Hydroformylation of 2 gave isoaldehydes 3 in high regio- and enantioselectivities (Scheme 2 and Table). Reduction of the aldehydes 3 with NaBH4 successfully afforded the corresponding alcohols 5 without loss of enantiomeric purity (Scheme 3).
Type II intramolecular [5+2] cycloaddition: Facile synthesis of highly functionalized bridged ring systems
Mei, Guangjian,Liu, Xin,Qiao, Chuang,Chen, Wei,Li, Chuang-Chuang
, p. 1754 - 1758 (2015)
A type II intramolecular oxidopyrylium-mediated [5+ 2] cycloaddition reaction allows the efficient and diastereoselective formation of various highly functionalized and synthetically challenging bridged seven-membered ring systems (such as bicyclo[4.4.1]undecane, bicyclo[4.3.1]decane, bicyclo[5.4.1]dodecane, and bicyclo[6.4.1]]tridecane). This simple, thermal, direct transformation has a broad substrate scope and is high yielding, with high functional-group tolerance and unique endo selectivity. The highly strained tricyclic cores of ingenol mebutate (picato) and cyclocitrinol are synthesized efficiently and diastereoselectively using this methodology.
Anodic coupling reactions: Exploring the generality of Curtin-Hammett controlled reactions
Redden, Alison,Moeller, Kevin D.
, p. 1678 - 1681 (2011)
Intramolecular anodic olefin coupling reactions can be compatible with the presence of dithioketal protecting groups even though the dithioketal oxidizes at a lower potential than either of the groups participating in the cyclization. In such cases, product formation is controlled by the Curtin-Hammett Principle. In this study, the generality of such reactions is examined along with the use of alternative reaction conditions to suppress unwanted side reactions.
Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades
Bower, John F.,Caiger, Lewis,García-Cárceles, Javier,Hazelden, Ian R.,Jones, Benjamin T.,Langer, Thomas,Lewis, Richard J.
supporting information, p. 15593 - 15598 (2021/10/12)
Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
NOVEL PRENYLARENE COMPOUND AND USE THEREOF
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Paragraph 0043, (2013/03/26)
A compound represented by the general formula (C): (wherein R101 represents a substituted or unsubstituted aromatic heterocyclic group, R102, R103, R104 and R105 may be the same or different, and each
Gold(I)-catalyzed endo-selective intramolecular α-alkenylation of β-yne-furans: Synthesis of seven-membered-ring-fused furans and dft calculations
Dong, Zhe,Liu, Cheng-Hang,Wang, Yi,Lin, Mu,Yu, Zhi-Xiang
supporting information, p. 14157 - 14161 (2014/01/06)
Alkenylation of furans: An efficient gold-catalyzed endo-selective intramolecular α-alkenylation of β-alkyne-substituted furans has been developed to synthesize challenging seven-membered-ring-fused furans in good to excellent yields. Preliminary DFT calc
Concise synthesis and structure-activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge
Kotoku, Naoyuki,Fujioka, Shinichi,Nakata, Chiaki,Yamada, Masaki,Sumii, Yuji,Kawachi, Takashi,Arai, Masayoshi,Kobayashi, Motomasa
experimental part, p. 6673 - 6678 (2011/09/30)
Structure-activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration.
Anodic coupling reactions: A sequential cyclization route to the arteannuin ring skeleton
Wu, Honghui,Moeller, Kevin D.
, p. 4599 - 4602 (2008/03/12)
(Chemical Equation Presented) A pair of intramolecular anodic olefin coupling reactions has been used to construct the arteannuin ring skeleton. Both coupling reactions took advantage of a furan ring as one of the coupling partners. In the first, it was found that an enol ether derived from an aldehyde was not an effective initiating group for the reaction. Instead, the cyclization benefited strongly from the use of a N,O-ketene acetal initiating group. In the second cyclization, an endocyclic enol ether was coupled to the furan ring. This second electrolysis reaction generated the key tetrasubstituted carbon at the center of the arteannuin ring skeleton.
Microwave-mediated claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring 1,4-benzoquinones. The first syntheses of verapliquinones A and B and panicein A
Davis, Christopher J.,Hurst, Timothy E.,Jacob, Aouregan M.,Moody, Christopher J.
, p. 4414 - 4422 (2007/10/03)
The naturally occurring 1,4-benzoquinones 2-methoxy-6-propyl-1,4- benzoquinone (1), 2-methoxy-6-pentyl-1,4-benzoquinone (primin 2), 2-methoxy-6-pentadecyl-1,4-benzoquinone (3), 2-methoxy-6-heptadecyl-l,4- benzoquinone (dihydroirisquinone, pallasone B; 4) were synthesized by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 10, followed by hydrogenation of the side chain alkene, and oxidation to the quinone. The Claisen-based methodology was extended to the first synthesis of the marine benzoquinones verapliquinones A and B (5 and 6), and panicein A (7). Isoarnebifuranone (9) was also synthesized by a similar strategy.
