13395-71-6Relevant articles and documents
Protecting-Group-Free Syntheses of ent-Kaurane Diterpenoids: [3+2+1] Cycloaddition/Cycloalkenylation Approach
Hong, Benke,Hu, Dachao,Kadonaga, Yuichiro,Lei, Xiaoguang,Tang, Ruyao,Wang, Jin
, p. 2238 - 2243 (2020)
The Yu's Rh-catalyzed [3+2+1] cycloaddition followed by a Pd-mediated 5-endo cycloalkenylation is shown to be a general and powerful approach for efficient construction of the tetracyclic core structure of ent-kaurane diterpenoids. The utility of this strategy was further demonstrated by concise and protecting-group-free total syntheses of ent-1α-hydroxykauran-12-one, 12-oxo-9,11-dehydrokaurene, and 12α-hydroxy-9,11-dehydrokaurene.
Highly Active Cooperative Lewis Acid—Ammonium Salt Catalyst for the Enantioselective Hydroboration of Ketones
Titze, Marvin,Heitk?mper, Juliane,Junge, Thorsten,K?stner, Johannes,Peters, René
supporting information, p. 5544 - 5553 (2021/02/05)
Enantiopure secondary alcohols are fundamental high-value synthetic building blocks. One of the most attractive ways to get access to this compound class is the catalytic hydroboration. We describe a new concept for this reaction type that allowed for exceptional catalytic turnover numbers (up to 15 400), which were increased by around 1.5–3 orders of magnitude compared to the most active catalysts previously reported. In our concept an aprotic ammonium halide moiety cooperates with an oxophilic Lewis acid within the same catalyst molecule. Control experiments reveal that both catalytic centers are essential for the observed activity. Kinetic, spectroscopic and computational studies show that the hydride transfer is rate limiting and proceeds via a concerted mechanism, in which hydride at Boron is continuously displaced by iodide, reminiscent to an SN2 reaction. The catalyst, which is accessible in high yields in few steps, was found to be stable during catalysis, readily recyclable and could be reused 10 times still efficiently working.
Method for producing cyclolavandulol and derivative thereof
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Paragraph 0077; 0078; 0079; 0080; 0081; 0082; 0083-0088, (2016/11/24)
The present invention easily, efficiently, and selectively produces a prescribed compound. More specifically, the present invention provides a method for producing (2,4,4-trimethyl-2-cyclohexene)methanol, said method at least comprising: a step for obtain
METHOD FOR PRODUCING CYCLOLAVANDULOL AND DERIVATIVE THEREOF
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Paragraph 0066-0073, (2016/08/29)
A targeted compound is produced simply, efficiently and selectively. Specifically provided are a method for producing (2,4,4-trimethyl-2-cyclohexene)methanol, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexenone (1) to o
METHODS FOR PRODUCING BETA-CYCLOLAVANDULAL AND DERIVATIVE OF SAME
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Paragraph 0083; 0084; 0085; 0086; 0087; 0088; 0089-0091, (2016/08/29)
Target compounds are synthesized simply, efficiently and selectively. More specifically, provided are a method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde, comprising the steps of: reacting the carbonyl group of 2,4,4-trimethyl-2-cyclohexeno
Method for producing [beta]-cyclolavandulal and derivative of same
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Paragraph 0095; 0096; 0097; 0098; 0099; 0100-0106, (2016/12/22)
A given compound is synthesized simply, efficiently, and selectively. Specifically, provided are a method for producing (2,4,4-trimethyl-1-cyclohexene)carbaldehyde including at least a step for obtaining a 2,4,4-trimethyl-2-cyclohexenylidene methyl ether compound (2) by reacting the carbonyl groups of 2,4,4-trimethyl-2-cyclohexenone (1) and a step for obtaining (2,4,4-trimethyl-1-cyclohexene)carbaldehyde (3) by hydrolyzing (2), a method for producing (2,4,4-trimethyl-1-cyclohexene)methanol including at least a step for obtaining (2,4,4-trimethyl-1-cyclohexene)methanol (4) by reducing (3), and a method for producing a (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound including at least a step for obtaining a (2,4,4-trimethyl-1-cyclohexenyl)methyl ester compound (5) by esterifying (4).
Synthesis, chemical reactivity as michael acceptors, and biological potency of monocyclic cyanoenones, novel and highly potent anti-inflammatory and cytoprotective agents(1)
Zheng, Suqing,Santosh Laxmi,David, Emilie,Dinkova-Kostova, Albena T.,Shiavoni, Katherine H.,Ren, Yanqing,Zheng, Ying,Trevino, Isaac,Bumeister, Ronald,Ojima, Iwao,Wigley, W. Christian,Bliska, James B.,Mierke, Dale F.,Honda, Tadashi
supporting information; body text, p. 4837 - 4846 (2012/07/03)
Novel monocyclic cyanoenones examined to date display unique features regarding chemical reactivity as Michael acceptors and biological potency. Remarkably, in some biological assays, the simple structure is more potent than pentacyclic triterpenoids (e.g
Enantioselective microbial oxidation of allyl alcohols
Matsumoto, Kazutsugu,Kawabata, Yoichi,Okada, Satoshi,Takahashi, Jun,Hashimoto, Key,Nagai, Yuto,Tatsuta, Junichi,Hatanaka, Minoru
, p. 1428 - 1429 (2008/03/18)
A new route to the optically active allyl alcohols by microbial oxidation is disclosed. Yamadazyma farinosa IFO 10896, a yeast, efficiently catalyzes the enantioselective oxidation of allyl alcohols to afford the corresponding optically active alcohols as the remaining substrates. This reaction is applicable to both cyclic and acyclic compounds. Copyright
Process for the preparation of cyclic ketones
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, (2008/06/13)
The invention provides a process for the preparation of cyclic ketones of the general formula STR1 in which R represents an optionally substituted alkyl or cycloalkyl group and R 1 and R 2 independently represent an optionally substituted alkyl, cycloalkyl or aryl group, which comprises heating a compound of the general formula STR2 in which X represents a chlorine or bromine atom and R is as defined above, with a compound of the general formula STR3 in which R 1 and R 2 are as defined above, in the presence of an organic acid.Certain cyclic ketones of formula (I) are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.
LIMITATIONS IN THE APPLICATION OF ANIONIC OXY-COPE SIGMATROPY TO ELABORATION OF THE FORSKOLIN NUCLEUS
Paquette, Leo A.,Oplinger, Jeffrey A.
, p. 107 - 124 (2007/10/02)
The functionalized bicyclooctenone 6 has been synthesized in four steps from 2,4,4-trimethyl-2-cyclohexenone.This ketone undergoes 1,2-addition with 6-lithiodihydropyran to deliver alcohols 16 and 17 in a 1:1.8 ratio.The potassium salt of 17 experi