- Erratum: Removal of the E-Olefin Barrier of Humulene Leading to Unnatural Terpenoid-like Skeletons (Organic Letters (2018) 20, 22, (7313-7320) DOI: 10.1021/acs.orglett.8b03259)
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The structures of compounds 11 and 12 shown in Figure 2A were corrected by changing the relative configurations, although the structures in the Supporting Information were correct. Figure 2A is corrected as follows: The absolute configurations of compounds 15-19 drawn in Figure 3A and in the Supporting Information were corrected. Although the relative configurations shown in the Supporting Information were correct, the wrong assignment is because of drawing the absolute configuration at the C-6 position of 15- 17 in reverse. The corrected Figure 3A is as follows and and the revised Supporting Information with the corrected structures for compounds 15-17 is included with this Correction.
- Nishimura, Takehiro,Kawai, Junya,Oshima, Yoshiteru,Kikuchi, Haruhisa
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supporting information
p. 1241 - 1241
(2019/05/16)
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- Removal of the E-Olefin Barrier of Humulene Leading to Unnatural Terpenoid-like Skeletons
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An unnatural terpenoid scaffold containing a bicyclo[5.4.0]undecane moiety, as well as a salvialane skeleton based on an intramolecular C-C bond formation strategy were synthesized. Such a strategy was made possible by the removal of strained E-olefin conformations of the humulene skeleton. Some compounds were identified to show PPARα antagonist activity.
- Nishimura, Takehiro,Kawai, Junya,Oshima, Yoshiteru,Kikuchi, Haruhisa
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supporting information
p. 7317 - 7320
(2018/11/25)
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- Where is the Oxygen? Structural Analysis of α-Humulene Oxidation Products by the Crystalline Sponge Method
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Crystal structures of α-humulene, a cyclic sesquiterpene, and its oxidized subproducts, were analyzed by the crystalline sponge method. Regio- and stereochemistry, including absolute configuration when a chiral oxidant was applied, and the stable conformations of all the scaffold-related compounds were successfully determined for samples on a 5-50 μg scale.
- Zigon, Nicolas,Hoshino, Manabu,Yoshioka, Shota,Inokuma, Yasuhide,Fujita, Makoto
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supporting information
p. 9033 - 9037
(2015/08/03)
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- Simple, chemoselective, catalytic olefin isomerization
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Catalytic amounts of Co(SaltBu,tBu)Cl and organosilane irreversibly isomerize terminal alkenes by one position. The same catalysts effect cycloisomerization of dienes and retrocycloisomerization of strained rings. Strong Lewis bases like amines and imidazoles, and labile functionalities like epoxides, are tolerated.
- Crossley, Steven W. M.,Barabé, Francis,Shenvi, Ryan A.
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supporting information
p. 16788 - 16791
(2015/01/09)
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- A stable rearrangement product of humulene-4,5-epoxide
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Humulene-4,5-monoepoxide, 1, may rearrange to the cyclopropyl diol 2 during chromatography over silica. The rearrangement can be reversed with acid.
- Carman, Raymond M.
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p. 1441 - 1442
(2008/09/20)
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- Transformations of α-Humulene and Some Its Monoepoxy Derivatives over Solid Acid Catalysts. Epoxidation of α-Humulene
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2,3- and 6,7-Epoxy derivatives of α-humulene in liquid superacids at low temperatures and over solid catalysts at room temperature undergo isomerizations whose direction is determined by conformational factors.
- Khomenko,Zenkovets,Barkhash
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p. 595 - 600
(2007/10/03)
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- Hydrolysis and Reversible Isomerization of Humulene Epoxides II and III
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The hydrolysis reactions of humulene epoxide II (3) and humulene epoxide III (4) were studied on aqueous solution at pH 4.0.Twelve compounds from the hydrolysis of humulene epoxide II and 16 from humulene epoxide III were separated and identified.All of the compounds identified from hydrolyis of 3 also were found among the hydrolysis products of 4.A reversible transformation between these two epoxides proceeding through a bicyclic diol (15) as intermediate is responsible for producing the same products.Hydrolysis reactions further yielded diols and a number of different ring systems.The apparent intermediacy of carbocations also led to several elimination reaction products.Among the products identified from these epoxides, six have not been reported before.These are 1,5,8,8-tetramethyl-12-oxa-5-tricyclo6,9>dodecene (1), 4,8,11,11-tetramethyl-8-tricyclo2,5>undecen-5-ol (5), stereoisomers of 2,6,6,9-tetramethyltricyclo2,4>undecane-5,9-diol (10, 14), 1,5,8,8-tetramethyl-8-bicycloundecene-2,9-diol (15), and the stereoisomeric pair 4,8,11,11-tetramethyltricyclo2,4>undecane-5,9-diol (16).
- Yang, Xiaogen,Deinzer, Max L.
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p. 4717 - 4722
(2007/10/02)
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