868756-10-9Relevant academic research and scientific papers
Total synthesis of (3R,5R) and (3R,5S)-sonnerlactones
Sanaboina, Chakrapani,Chidara, Sridhar,Jana, Samaresh,Eppakayala, Laxminarayana
, p. 1767 - 1770 (2016/04/05)
In this Letter, an enantioselective synthesis of (3R,5R)-sonnerlactone and (3R,5S)-sonnerlactone have been described. Stereochemistry at C-5 position was fixed using a suitable proline catalyzed reaction during the synthesis of aliphatic segment. To accom
Efficient synthesis of anacardic acid analogues and their antibacterial activities
Mamidyala, Sreeman K.,Ramu, Soumya,Huang, Johnny X.,Robertson, Avril A.B.,Cooper, Matthew A.
, p. 1667 - 1670 (2013/04/10)
Anacardic acid derivatives exhibit a broad range of biological activities. In this report, an efficient method for the synthesis of anacardic acid derivatives was explored, and a small set of salicylic acid variants synthesised retaining a constant hydrophobic element (a naphthyl tail). The naphthyl side chain was introduced via Wittig reaction and the aldehyde installed using directed ortho-metalation reaction of the substituted o-anisic acids. The failure of ortho-metalation using unprotected carboxylic acid group compelled us to use directed ortho-metalation in which a tertiary amide was used as a strong ortho-directing group. In the initial route, tertiary amide cleavage during final step was challenging, but cleaving the tertiary amide before Wittig reaction was beneficial. The Wittig reaction with protected carboxylic group (methyl ester) resulted in side-products whereas using sodium salt resulted in higher yields. The novel compounds were screened for antibacterial activity and cytotoxicity. Although substitution on the salicylic head group enhanced antibacterial activities they also enhanced cytotoxicity.
Probing the reactivity of o-phthalaldehydic acid/methyl ester: Synthesis of N-isoindolinones and 3-arylaminophthalides
Mamidyala, Sreeman K.,Cooper, Matthew A.
, p. 8407 - 8409 (2013/09/23)
A new method for the synthesis of N-substituted isoindolinones and 3-arylaminophthalides was developed through aza-Wittig/cyclisation. The reaction of o-phthalaldehydic acid methyl ester with benzylic, aromatic and aliphatic azides gave N-isoindolinones w
Synthesis of a regioisomeric analogue of the 3C-protease inhibitor?thysanone via a Hauser annulation strategy
Brimble, Margaret A.,Houghton, Scott I.,Woodgate, Paul D.
, p. 880 - 887 (2007/10/03)
Hauser annulation of 3-cyano-5,7-dimethoxy-(3H)-isobenzofuran-1-one 4 with ethyl acrylate as a method to access activated naphthoquinone 3, a key intermediate for the synthesis of thysanone 1, proved unreliable. In contrast to this, Hauser annulation of r
Synthesis of the phthalide-containing anti-Helicobacter pylori agents CJ-13,015, CJ-13,102, CJ-13,103, CJ-13,104 and CJ-13,108
Brimble, Margaret A.,Flowers, Christopher L.,Hutchinson, James K.,Robinson, James E.,Sidford, Matthew
, p. 10036 - 10047 (2007/10/03)
Flexible racemic syntheses of the phthalide-containing antibiotics CJ-13,015, CJ-13,102, CJ-13,103, CJ-13,104 and CJ-13,108 that inhibit Helicobacter pylori have been carried out in a convergent fashion by Wittig coupling of a phthalide-containing aldehyd
A synthetic approach to sporotricale methylether
Dallavalle, Sabrina,Nannei, Raffaella,Merlini, Lucio,Bava, Adriana,Nasini, Gianluca
, p. 2676 - 2678 (2007/10/03)
A synthetic approach to sporotricale methylether, a metabolite of the fungus Sporotrichum laxum with inhibitory activity against Helicobacter pylori, is described. The synthesis relies on the condensation of 13-hydroxy-10- oxotetradecanal, prepared via reaction of a sulfone-activated moiety with valerolactone, with diethyl 3,5-dimethoxyphthalide-7-phosphonate. Georg Thieme Verlag Stuttgart.
