65376-05-8Relevant articles and documents
Fused-ring nitrogen and sulfur heterocycles by a tandem SN2-Michael addition reaction
Bunce, Richard A.,Kotturi, Sharadsrikar V.,Peeples, Christopher J.,Holt, Elizabeth M.
, p. 1049 - 1054 (2002)
A tandem SN2-Michael addition reaction has been developed for the synthesis of cis- and trans-fused nitrogen and sulfur heterocycles from the cis and trans isomers of ethyl (±)-(2E)-3-[2-(iodomethyl)cyclohexyl]-2-propenoate. Octahydro-1H-isoindole-1-acetic acid and octahydrobenzo[c]thiophene-1-acetic acid derivatives have been prepared and their stereochemistries elucidated using NMR and X-ray crystallographic methods. Cyclization substrates for both the cis- and the trans-fused rings are readily available in four steps from known compounds. Yields for the cyclization range from 80-85% and stereochemical selectivities with respect to the side chain vary from 12.5-16:1 for the cis-fused structures to 6-7.5:1 for the transfused structures. Steric interactions in the transition states for ring closure are proposed to rationalize the observed preferences.
Preparation method for lurasidone hydrochloride
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, (2017/08/30)
The invention discloses a preparation method for lurasidone hydrochloride. According to the preparation method, trans-1,2-cyclohexanedicarboxylic acid (SM-1) is used as a raw material and subjected to resolution, methyl esterification, reduction, methylsulfonylation, condensation, recrystallization and salt formation so as to eventually obtain lurasidone hydrochloride. The preparation method provided by the invention greatly reduces production cost and has the characteristics of high product yield, easy operation, low toxicity and suitability for industrial large-scale production.
Truncated borrelidin analogues: Synthesis by sequential cross metathesis/olefination for the southern fragment and biological evaluation
Gündemir-Durmaz, Tülay,Schmid, Fabian,El Baz, Yana,H?usser, Annette,Schneider, Carmen,Bilitewski, Ursula,Rauhut, Guntram,Garnier, Delphine,Baro, Angelika,Laschat, Sabine
supporting information, p. 8261 - 8269 (2016/09/09)
The construction of novel borrelidin analogues is reported in which the northern fragment is truncated to a simple hydroxyundecanecarboxylate and the original cyclopentanecarboxylic acid in the southern fragment is replaced with different six-membered rings. The required precursors were prepared by cross metathesis of the appropriate carbocycle-based homoallylic alcohol with crotonaldehyde followed by HWE olefination of the resulting enal with bromocyanophosphonate. The key aldehyde for intramolecular cross coupling was accessible by oxidation of the hydroxy group of the linked undecanecarboxylate unit. Grignard mediated macrocyclization finally yielded the borrelidin related products. The investigation is complemented by SAR studies and quantum-chemical calculations.