80868-19-5Relevant academic research and scientific papers
Synthesis and NMR spectroscopic elucidation of four diastereoisomers of oxygenated bisabolane side chain
Hirai, Misaki,Miyazaki, Rurina,Mitsui, Kana,Kiuchi, Kota,Onuki, Hiroyuki,Hirota, Hiroshi,Kuroda, Chiaki
, p. 1035 - 1060 (2015)
Four possible stereoisomers of a model compound of highly O-bearing bisabolane sesquiterpenes were synthesized and their NMR spectra were compared. Starting from isopulegol, allylic oxidation and Grignard reaction afforded a mixture of alcohols at C(8), which was separated. After metathesis reaction, both α- and β-epoxides were obtained via non-stereoselective epoxidation, while VO(OiPr)3-catalyzed epoxidation afforded a single diastereoisomer selectively. NMR Spectra of twelve synthesized compounds, four stereoisomers of acetates, isobutyrates, and tiglates, were measured. A difference between C(8α)- and C(8β)-acyloxy isomers was observed in the δ-values of H-C(8) in CDCl3. Within the 8β-acyloxy compounds, the α- and the β-epoxides were distinguished by either the J-value of H-C(8) or the chemical shift of CH2(9). Within the 8α-acyloxy compounds, two epoxide isomers were distinguished by the J-value of H-C(10) in C6D6 or in CD3OD.
Total Synthesis of Ajudazol A by a Modular Oxazole Diversification Strategy
Essig, Sebastian,G?lz, Jan Philipp,Menche, Dirk,Von Schwarzenberg, Karin,Wollnitzke, Philipp
supporting information, (2020/09/02)
The total synthesis of the potent respiratory chain inhibitor ajudazol A was accomplished by a concise strategy in 17 steps (longest linear sequence). The modular approach was based on a direct oxazole functionalization strategy involving a halogen dance
Hydroalkylation of Olefins to Form Quaternary Carbons
Green, Samantha A.,Huffman, Tucker R.,McCourt, Ruairí O.,Van Der Puyl, Vincent,Shenvi, Ryan A.
supporting information, (2019/05/22)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.
Hydroalkylation of Olefins to Form Quaternary Carbons
Green, Samantha A.,Huffman, Tucker R.,McCourt, Ruairí O.,Van Der Puyl, Vincent,Shenvi, Ryan A.
supporting information, p. 7709 - 7714 (2019/05/22)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.
Directed hydrogenation of acyclic homoallylic alcohols: Enantioselective syntheses of (+)- and (-)-laurenditerpenol
Chittiboyina, Amar G.,Peddikotla, Prabhakar,Avery, Mitchell A.,Khan, Ikhlas A.
, p. 9223 - 9232 (2013/10/08)
Laurenditerpenol is the first marine natural product shown to inhibit hypoxia-inducible factor 1 (HIF-1) activation. Preclinical studies support that the inhibition of HIF-1 is one of the molecular targets for antitumor drug discovery. The synthetically c
Synthesis of thiabicyclic heterocycles through free radical cyclization of β-thioacrylates
Bilokin, Yaroslav V.,Melman, Artem,Niddam, Valérie,Benhamú, Bellinda,Bachi, Mario D.
, p. 3425 - 3437 (2007/10/03)
8-Aza-3-thiabicyclo[4.3.0]nonanes 7 and 8, 3-thiabicyclo[4.4.0]decanes 18, and 8-thiabicyclo[4.3.0]nonanes 31 were obtained from monocyclic precursors through free radical cyclizations involving a β-thioacrylate system as radical acceptor and a thionocarbonate as radical precursor. Oxidative sulfur extrusion in 3-thiabicyclo[4.4.0]decanes 18 afforded methyl (2-isopropenyl-5-methylcyclohexyl)-2-propenoates 35. (C) 2000 Elsevier Science Ltd.
