148515-21-3Relevant articles and documents
Enantioselective total synthesis of (+)-amabiline
Senter, Timothy J.,Fadeyi, Olugbeminiyi O.,Lindsley, Craig W.
, p. 1869 - 1871 (2012)
The first total synthesis of (+)-amabiline, an unsaturated pyrrolizidine alkaloid from Cynoglossum amabile, is reported. This convergent, enantioselective synthesis proceeds in 15 steps (10-step longest linear sequence) in 6.2% overall yield and features
Synthesis of the Dipeptide Hydroxyethylene Isostere of Leu-Val, a Transition State Mimic for the Control of Enzyme Function
Wuts, Peter G. M.,Putt, Sterling R.,Ritter, Allen R.
, p. 4503 - 4508 (1988)
Dipeptide isosteres have recently begun to attract attention because of their ability to mimic the transition states of proteolytic enzymes or to alter or enhance the function of regulatory peptides.We have developed a general approach that may be used to prepare a diverse array of dipeptide hydroxyethylene isosteres.As an example we have prepared a mimic of Leu-Val, the cleavage site of the enzyme renin.The sequence begins with leucinal 8. which is converted to the aldehyde 15ct by addition of vinylmagnesium bromide to form an allylic alcohol.This is converted to the acetonide, ozonized, and equilibrated to give the trans aldehyde 15t as the primary product.A Wadsworth-Emmons olefination fallowed by hydrogenation affords the ester 30 as a mixture of isomers.Hydrolysis of the acetonide and purification gives the desired lactone 26β in 23percent overall yield from BOC-leucinol.
Total synthesis of a novel 2-thiabicyclo[3.2.0]heptan-6-one analogue of penicillin N
Ferguson, Amanda C.,Adlington, Robert M.,Martyres, Domnic H.,Rutledge, Peter J.,Cowley, Andrew,Baldwin, Jack E.
, p. 8233 - 8243 (2003)
A route has been developed which allows synthesis of novel cyclobutanone analogues of penicillin. This is illustrated by the synthesis of (1R,4R,5R,5′R,7S)-(1b) and (1S,4S,5S,5′R,7R)-7-[5′ -amino-5′-carboxy]pentanamido]-2-thiabicyclo[3.2.0] heptan-6-one-4-carboxylate (1a), an analogue of penicillin N. The key steps in the synthesis were the formation of the bicyclic structure via a [2+2] cycloaddition and the introduction of nitrogen at C7 via an intramolecular nitrene insertion.
Synthesis and olfactoric activity of side-chain modified β-santalol analogues
Buchbauer, Gerhard,Sunara, Aneta,Weiss-Greiler, Petra,Wolschann, Peter
, p. 673 - 683 (2001)
Three osmophoric points have been postulated to be necessary for the sandalwood scent of β-santalol derivatives. One of these points, close to the hydroxyl group, is highly specific on the stereochemistry and, in particular, on the molecular shape. The ro
Design, Synthesis, and Biological Evaluation of Novel Pyrimido[4,5-b]indole Derivatives against Gram-Negative Multidrug-Resistant Pathogens
Kong, Qidi,Pan, Wei,Xu, Heng,Xue, Yaru,Guo, Bin,Meng, Xin,Luo, Cheng,Wang, Ting,Zhang, Shuhua,Yang, Yushe
supporting information, p. 8644 - 8665 (2021/06/28)
Due to the poor permeability across Gram-negative bacterial membranes and the troublesome bacterial efflux mechanism, only a few GyrB/ParE inhibitors with potent activity against Gram-negative pathogens have been reported. Among them, pyrimido[4,5-b]indol
P2X4 RECEPTOR MODULATING COMPOUNDS
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Paragraph 00256, (2015/06/25)
Provided herein are P2X4 receptor modulating compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, including but not limited to, chronic pain, neuropathy, inflammatory diseases and central nervous system disorders.
A Total synthesis of aliskiren starting from D-Tartrate diester
Kim, Ji Hei,Ko, Soo Y.
, p. 3777 - 3781 (2014/01/17)
A formal total synthesis of aliskiren was accomplished. A key in our synthesis was to use the symmetric ciscisoid-Cis-Bis-Lactone 3' as a precursor, which was prepared from D-tartrate diester. Appending the end groups and functional group transformations completed the synthesis.
Investigation on lewis acid mediated diels-alder reactions of 2-phosphono-2-alkenoates. Application to total synthesis of (±)-α- alasken-8-one via reductive alkylation of resulting adduct
Liao, Chuan-Cheng,Zhu, Jia-Liang
body text, p. 7873 - 7884 (2010/01/16)
(Chemical Equation Presented) The Lewis acid mediated Diels-Alder reactions of three 2-phosphono-2-alkenoates including triethyl 2-phosphonoacrylate (1), triethyl 2-phosphonobut-2-enoate (2), and ethyl 2-(diethoxyphosphono)-3- methylbut-2-enoate (3) have been investigated. Of several Lewis acids tested, tin(IV) chloride was shown to be the most effective at enhancing the regio- and stereoselectivity of the reactions of 1 with the electron-rich dienes to result in the formation of the single regio- and/or stereoisomers in good yields. Bearing the β methyl group(s), 2 displayedmuch less reactivity than 1 while 3 was completely unreactive under the study's conditions. Throughout the investigation, we found that the cycloadditions of 2, especially of the Z-isomer, could be efficiently induced by using zinc chloride at elevated temperatures. Furthermore, a lithium naphthalenide (LN)-induced reductive alkylation process was applied to the resulting Diels-Alder adducts 4 to allow the phosphono group at the quaternary carbon centers to be replaced by various alkyl groups to afford the alkyl-substituted esters 12, therefore practically turning 1 and 2 into the useful synthetic equivalents of the corresponding 2-alkyl 2-alkenoates that usually display poor Diels-Alder reactivity. Application of this combined operation has facilitated the total synthesis of the sesquiterpene natural product α-alasken-8-one (8) in racemic form.
CHEMICAL COMPOUNDS
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Page/Page column 119, (2010/02/15)
The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel naphthalene compounds that are particularly useful for selective estrogen receptor modulation.
Absolute configuration and synthesis of β- and δ-lactones present in the pheromone system of the giant white butterfly Idea leuconoe
Stritzke, Katja,Schulz, Stefan,Nishida, Ritsuo
, p. 3884 - 3892 (2007/10/03)
Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the β-lactones la and lb is based on a controlled C-C coupling by a Horner-Wadsworth-Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the δ-lactone 3b uses an enantioselective hydrogenation of a dioxoalkanoate precursor. The absolute configurations of the natural lactones 1a, 1b and 3b were determined by gas chromatography on a chiral stationary phase. Both 1a and 1b are of (S,S) configuration, suggesting their biosynthetic origin from (-)-viridifloric acid (7a) or (-)norviridifloric acid (7b), respectively. In contrast, natural 3b is a mixture of all enantiomers, in which the (5S,7S) enantiomer dominates. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
