{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T03:08:21Z","timestamp":1780369701205,"version":"3.54.1"},"reference-count":43,"publisher":"Wiley","issue":"13","license":[{"start":{"date-parts":[[2013,7,9]],"date-time":"2013-07-09T00:00:00Z","timestamp":1373328000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Labelled Comp Radiopharmac"],"published-print":{"date-parts":[[2013,11]]},"abstract":"<jats:p>Deuterium\u2010labeled biologically active compounds are gaining importance because they can be utilized as tracers or surrogate compounds to understand the mechanism of action, absorption, distribution, metabolism, and excretion. Deuterated drug molecules (heavy drugs) become novel as well as popular because of better stability and bioavailability compared with their hydrogen analogs. Labeling of organic molecules with deuterium at specific positions is thus gaining popularity. In this work, we have exploited a highly regioselective and enantioselective direct Michael addition of methyl\u2010<jats:italic>d<\/jats:italic><jats:sub>3<\/jats:sub> alkyl ketones to dimethyl(phenyl)silylmethylene malonate that was catalyzed by (<jats:italic>S<\/jats:italic>)\u2010<jats:italic>N<\/jats:italic>\u2010(2\u2010pyrrolidinylmethyl)pyrrolidine\/trifluoroacetic acid\/ D<jats:sub>2<\/jats:sub>O combination with high yield and isotopic purity. The 5,5\u2010dideutero\u20104\u2010dimethyl(phenyl)silyl\u20106\u2010undecyl\u2010tetrahydropyran\u20102\u2010one was obtained from the adduct of methyl\u2010<jats:italic>d<\/jats:italic><jats:sub>3<\/jats:sub> undecanyl ketone and dimethyl(phenyl)silylmethylene malonate by a silicon controlled diastereoselective ketone reduction, lactonization, and deethoxycarbonylation. The dideuterated silylated tetrahydropyran\u20102\u2010one is the precursor for <jats:italic>geminal<\/jats:italic> <jats:sup>2<\/jats:sup>H<jats:sub>2<\/jats:sub>\u2010labeled (+)\u20104\u2010hydroxy\u20106\u2010undecyl\u2010tetrahydropyran\u20102\u2010one, an advanced intermediate for <jats:italic>gem<\/jats:italic>\u2010dideutero (\u2013)\u2010tetrahydrolipstatin and (+)\u2010\u03b4\u2010hexadecanolide syntheses.<\/jats:p>","DOI":"10.1002\/jlcr.3081","type":"journal-article","created":{"date-parts":[[2013,7,9]],"date-time":"2013-07-09T08:41:29Z","timestamp":1373359289000},"page":"649-654","source":"Crossref","is-referenced-by-count":10,"title":["A facile synthesis of 5,5\u2010dideutero\u20104\u2010dimethyl(phenyl)silyl\u20106\u2010undecyl\u2010tetrahydropyran\u20102\u2010one as a deuterium labeled synthon for (\u2212)\u2010tetrahydrolipstatin and (+)\u2010\u03b4\u2010hexadecanolide"],"prefix":"10.1002","volume":"56","author":[{"given":"Sandip J.","family":"Wagh","sequence":"first","affiliation":[{"name":"Bio\u2010Organic Division Bhabha Atomic Research Centre  Trombay Mumbai 400085 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raghunath","family":"Chowdhury","sequence":"additional","affiliation":[{"name":"Bio\u2010Organic Division Bhabha Atomic Research Centre  Trombay Mumbai 400085 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sulekha","family":"Mukhopadhyay","sequence":"additional","affiliation":[{"name":"Chemical Engineering Division Bhabha Atomic Research Centre  Trombay Mumbai 400085 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sunil K.","family":"Ghosh","sequence":"additional","affiliation":[{"name":"Bio\u2010Organic Division Bhabha Atomic Research Centre  Trombay Mumbai 400085 India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,7,9]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1124\/dmd.31.12.1481"},{"key":"e_1_2_7_3_1","doi-asserted-by":"crossref","first-page":"12349","DOI":"10.1016\/S0021-9258(19)38353-X","volume":"265","author":"Hall L. 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