33375-08-5Relevant articles and documents
Picrotoxin-like lactones
McChesney,Wycpalek
, p. 1131 - 1134 (1983)
Preparation of some simple lactone analogues of picrotoxin and their biological evaluation is reported. Certain analogues possessed activity, but at potencies insufficient to warrant further work.
Enantiospecific total synthesis of both enantiomers of 2-thiocyanatoneopupukeanane from (R)-carvone
Srikrishna,Gharpure, Santosh J.
, p. 3191 - 3193 (2000)
Enantiospecific total synthesis of both enantiomers of 2-thiocyanatoneopupukeanane from (R)-carvone, employing an intramolecular rhodium carbenoid C-H insertion reaction as the key step, was discussed. Reduction of ketone using either sodium borohydride o
High-Throughput Synthesis of (S)-α-Phellandrene through Three-Step Sequential Continuous-Flow Reactions
Miller, Samuel J.,Ishitani, Haruro,Furiya, Yuichi,Kobayashi, Shū
supporting information, p. 192 - 198 (2021/02/05)
The combination of continuous-flow processing with heterogeneous catalysts allows for efficient, sustainable, multistep synthesis. Here, we report the continuous-flow synthesis of a valuable terpene product, phellandrene, from a readily available natural feedstock. The protocol consists of selective hydrogenation using a highly active and stable supported platinum catalyst, dehydrative hydrazone formation, followed by the Shapiro reaction. Appropriate design of the reactor allowed for high productivity and space-time yield. Phellandrene was synthesized on a 30-g scale over 6 h, giving high yields, purity, and productivity.
On the Diastereoselectivity of the Complexation of Ketopinic Acid-Derived 2-Acyloxy-1,3-cyclohexadienes and the Configurational Stability of Dienol-Fe(CO)3Complexes. A Case Study
Adler, Andreas,Botov, Svetlana,Hemmersbach, Lars,Neud?rfl, J?rg-Martin,Romanski, Steffen,Schmalz, Hans-Günther
supporting information, p. 2909 - 2914 (2021/08/30)
In the course of an attempt to synthesize 2-acyloxycyclohexa-1,3-diene-Fe(CO)3 complexes in nonracemic form, we reinvestigated the "fully diastereoselective"Fe(CO)3 complexation of (S,S)-2-ketopinoyloxy-1,3-cyclohexadiene, which had been described by Yeh and co-workers (Organometallics 2001, 20, 289-295). However, after cleaving off the chiral auxiliary unit, we only obtained racemic complexes, also for a related substrate. For this reason, we performed control experiments to exclude possible racemization mechanisms and confirmed the configurational integrity of the dienol-Fe(CO)3 intermediates using stereochemically defined dihydrocarvone-derived complexes. We finally could show that the complexation described by Yeh actually proceeds without any detectable diastereoselectivity. At the end, the virtually inseparable diastereomers of the chiral complexation products could be distinguished by careful NMR and chiral HPLC analyses.
Design and Synthesis of A-Ring Simplified Pyripyropene A Analogues as Potent and Selective Synthetic SOAT2 Inhibitors
Ohtawa, Masaki,Arima, Shiho,Ichida, Naoki,Terayama, Tomiaki,Ohno, Hironao,Yamazaki, Takaya,Ohshiro, Taichi,Sato, Noriko,Omura, Satoshi,Tomoda, Hiroshi,Nagamitsu, Tohru
supporting information, p. 411 - 421 (2018/02/06)
Currently, pyripyropene A, which is isolated from the culture broth of Aspergillus fumigatus FO-1289, is the only compound known to strongly and selectively inhibit the isozyme sterol O-acyltransferase 2 (SOAT2). To aid in the development of new cholester
Total Synthesis of Adunctin B
Dethe, Dattatraya H.,Dherange, Balu D.
, p. 3392 - 3396 (2018/03/23)
Total synthesis of (±)-adunctin B, a natural product isolated from Piper aduncum (Piperaceae), has been achieved using two different strategies, in seven and three steps. The efficient approach features highly atom economical and diastereoselective Friedel-Crafts acylation, alkylation reaction and palladium catalyzed Wacker type oxidative cyclization.
NOVEL PHARMACEUTICAL COMPOUND HAVING INHIBITORY ACTIVITY AGAINST CHOLESTEROL ACYLTRANSFERASE ISOZYME 2 (ACAT 2)
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Paragraph 0136-0137, (2016/10/08)
PROBLEM TO BE SOLVED: To provide a compound having an action mechanism different from a statin-based medicine and an inhibitory activity against cholesterol acyltransferase isozyme 2 (ACAT 2), and a pharmaceutical composition comprising the compound. SOLU
Microwave assisted bi-functional activation of β-bromo-tert-alcohols
Kannan, Nandini,Rangaswamy, Manjunatha Javagal,Kemapaiah, Bettadaiah Bheemanakere
, p. 1405 - 1410 (2015/11/09)
Microwave-assisted dehydration-oxidation of β-bromo-tert-alcohols to afford 2,3-unsaturated ketones in good yield is reported. The reaction of substrates with DMSO in 1:1 ratio (w/v) is promoted by ZnS in a solvent-free condition. A concurrent bi-functional activation of trans-vicinal bromo- and hydroxyl groups with ZnS is elucidated. This is a new observation under microwave and applies to β-bromo-tert-alcohols derived from 1,4-disubstitued-1-cyclohexenes. It is very useful in the synthesis of 2,3-unsaturated ketones derived from monoterpenes which are valuable flavour compounds. [Figure not available: see fulltext.]
Selective carvone hydrogenation to dihydrocarvone over titania supported gold catalyst
Demidova,Suslov,Simakova,Simakova,Volcho,Salakhutdinov,Murzin
, p. 189 - 194 (2015/03/14)
Selective hydrogenation of natural carvone to industrially valuable dihydrocarvone was carried out at 100°C under hydrogen pressure over a 1.9wt.% Au/TiO2 catalyst. The gold catalyst has demonstrated high activity as well as stereo- and chemoselectivity in conjugated C=C double bond hydrogenation with predominant formation of trans-dihydrocarvone. The catalytic activity and trans-to cis-isomers ratio were shown to strongly depend on the solvent. In a range of C1 - C3 alcohol solvents both catalytic activity and trans-to cis-dihydrocarvone ratio increased following the order: 2-propanol a nearly complete carvone conversion (90%) after 13h in the case of methanol, with the trans-to cis-dihydrocarvone ratio being about 1.8. Based on the transition state theory a quantitative description of trans-to cis-dihydrocarvone ratio variations in different solvents was made.
METHOD FOR PRODUCING COMPOUND WITH CARBONYL GROUP BY USING RUTHENIUM CARBONYL COMPLEX HAVING TRIDENTATE LIGAND AS DEHYDROGENATION OXIDATION CATALYST
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Page/Page column 46-48, (2012/11/07)
Provided by the present invention is a method for efficient oxidation of alcohols by using, as a catalyst for dehydrogenation oxidation, a ruthenium complex which can be easily produced and easily handled and is obtainable at a relatively low cost. The invention relates to a method of producing a compound having a carbonyl group by dehydrogenation oxidation of alcohols by using as a catalyst the ruthenium carbonyl complex represented by the following general formula (1) RuXY(CO)(L) (1) (in the general formula (1), X and Y may be the same or different from each other and represent an anionic ligand, and L represents a tridentate aminodiphosphine ligand).
