01400nas a2200265 4500008004100000022001400041245008900055210006900144260010600213300001400319490000700333520039800340653002800738653002700766653002800793653002500821653002800846100002400874700002400898700002400922700002300946700002400969700002400993856011701017 2014 eng d a0040-403900aChiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid0 aChiron approach to formal synthesis of both antipodes of cis 3hy aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcNOV a6423-64260 v553 a

The efficient and practical formal syntheses of both enantiomers of cis 3-hydroxypipecolic acid were accomplished from cis aziridine-2-carboxylate as the common synthetic precursor. The key steps involved are stereo and regioselective aziridine ring opening, reductive cyclization and selective N-debenzylation over O-debenzylation reactions. (C) 2014 Elsevier Ltd. All rights reserved.

10a3-Hydroxypipecolic acid10aAziridine ring opening10aAziridine-2-carboxylate10aPiperidine alkaloids10aSelective debenzylation1 aChavan, Subhash, P.1 aKhairnar, Lalit, B.1 aChavan, Prakash, N.1 aDumare, Nilesh, B.1 aKalbhor, Dinesh, B.1 aGonnade, Rajesh, G. uhttps://library.ncl.res.in/content/chiron-approach-formal-synthesis-both-antipodes-cis-3-hydroxypipecolic-acid-001055nas a2200181 4500008004100000022001400041245007400055210006800129260010600197300001400303490000700317520035000324100002400674700002400698700002400722700002400746856010300770 2014 eng d a0957-416600aShort enantioselective total synthesis of (R)- and (S)-pipecolic acid0 aShort enantioselective total synthesis of R and Spipecolic acid aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDbPERGAMON-ELSEVIER SCIENCE LTDcSEP a1246-12510 v253 a

A convenient and practical total synthesis of (R)- and (S)-pipecolic acid has been achieved by utilizing chiral cis-aziridine-2-carboxylate as the common synthetic precursor. The synthesis involves regioselective reductive cleavage of the aziridine ring and Wittig olefination as key reactions. (C) 2014 Elsevier Ltd. All rights reserved.

1 aChavan, Subhash, P.1 aKhairnar, Lalit, B.1 aChavan, Prakash, N.1 aKalbhor, Dinesh, B. uhttps://library.ncl.res.in/content/short-enantioselective-total-synthesis-r-and-s-pipecolic-acid-000731nas a2200193 4500008004100000022001400041245011300055210006900168260000900237300001100246490000700257100002400264700002400288700002400312700002300336700002400359700002400383856013000407 2020 eng d a0040-403900aChiron approach to formal synthesis of both antipodes of cis 3-hydroxypipecolic acid (vol 55, pg 6423, 2014)0 aChiron approach to formal synthesis of both antipodes of cis 3hy cDEC  a1526440 v611 aChavan, Subhash, P.1 aKhairnar, Lalit, B.1 aChavan, Prakash, N.1 aDumare, Nilesh, B.1 aKalbhor, Dinesh, B.1 aGonnade, Rajesh, G. uhttps://library.ncl.res.in/content/chiron-approach-formal-synthesis-both-antipodes-cis-3-hydroxypipecolic-acid-vol-55-pg-642301085nas a2200241 4500008004100000022001400041245016100055210006900216260000900285300001100294490000700305520021100312653001600523653002400539653002000563653001900583653001700602100002400619700002300643700002200666700002400688856013100712 2021 eng d a0040-403900aApplication of allylic amine formation from aziridine-2-ol under appel reaction condition: synthesis of N-(tert-butoxycarbonyl)-D-vinyl glycine methyl ester0 aApplication of allylic amine formation from aziridine2ol under a cJUN  a1531190 v733 a

PPh3/I-2/imidazolde mediated allyl amine formation from aziridine-2-alcohol was explored for the synthesis of N-(tert-butoxycarbonyl)-D-vinyl glycine methyl ester. (C) 2021 Published by Elsevier Ltd.

10aAllyl amine10aAziridine-2-alcohol10aAziridinium ion10aBirch reaction10aRing opening1 aChavan, Subhash, P.1 aKawale, Sanket, A.1 aPatil, Niteen, B.1 aKalbhor, Dinesh, B. uhttps://library.ncl.res.in/content/application-allylic-amine-formation-aziridine-2-ol-under-appel-reaction-condition-synthesis01589nas a2200229 4500008004100000022001400041245014100055210006900196260000800265300001100273490000700284520076600291653001801057653002101075653002101096653002501117653001901142100002401161700002401185700002401209856012601233 2021 eng d a0040-402000aDivergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent0 aDivergent approach to the synthesis of balanol heterocycle and c cJAN a1317730 v803 a

Enantioselective synthesis of the hexahydroazepine core of (-)-balanol and formal synthesis of cis-3hydroxypipecolic acid from a common intermediate have been accomplished by a divergent path. The common intermediate was accessed from a favorably protected enantiomerically pure 2-amino-1,3,4-butanetriol (ABT) equivalent via oxidation and Wittig olefination. The synthesis of (-)-balanol heterocycle featured tandem reduction/acetal-deprotection/gamma-lactonization reaction and a one-pot azide reduction followed by seven membered aza-heterocycle formation while the route to cis-3-hydroxypipecolic acid highlighted the base induced piperidine ring formation and regioselective benzylidine-acetal cleavage. (C) 2020 Elsevier Ltd. All rights reserved.

10aAmino-alcohol10adesymmetrization10aHexahydroazepine10aPiperidine alkaloids10aProtein kinase1 aChavan, Subhash, P.1 aKalbhor, Dinesh, B.1 aGonnade, Rajesh, G. uhttps://library.ncl.res.in/content/divergent-approach-synthesis-balanol-heterocycle-and-cis-3-hydroxypipecolic-acid-based01145nas a2200169 4500008004100000022001400041245013500055210006900190260000900259300001600268490000600284520048300290100002400773700002400797700002400821856013000845 2022 eng d a2470-134300aRapid synthesis of the epi-biotin sulfone via tandem S,N-carbonyl migration/aza-michael/spirocyclization and haller-bauer reaction0 aRapid synthesis of the epibiotin sulfone via tandem SNcarbonyl m cMAY  a17215-172220 v73 a

A synthesis of 2-epi-biotin sulfone was accomplished from commercially available L-cysteine. The synthesis features an unprecedented tandem S,N-carbonyl migration/aza-Michael/spirocyclization reaction from an L-cysteine-derived enone with aq. ammonia, in which three new sigma bonds and two rings are formed. In addition, the synthesis includes a highly diastereoselective late-stage Haller-Bauer reaction of sulfone for direct introduction of the carbon side chain.

1 aChavan, Subhash, P.1 aKalbhor, Dinesh, B.1 aGonnade, Rajesh, G. uhttps://library.ncl.res.in/content/rapid-synthesis-epi-biotin-sulfone-tandem-sn-carbonyl-migrationaza-michaelspirocyclization01321nas a2200217 4500008004100000022001400041245009100055210006900146260000800215490000700223520058800230653001400818653002500832653002600857653001600883653002100899100002400920700002400944700002400968856011100992 2023 eng d a2193-580700aRapid bioinspired N-acyliminium ion strategy for the ABC core of the stemona alkaloids0 aRapid bioinspired Nacyliminium ion strategy for the ABC core of  cSEP0 v123 a

A concise and highly diastereoselective bioinspired key cationic cyclization strategy for the asymmetric synthesis of the tricyclic core of the (-)-stemoamide, together with 8,9-bis-epi-stemoamide has been described. The key N-acyliminium ion precursors were accessed from L-tartaric acid and L-malic acid respectively. The use of ethyl acetoacetate derived bifunctional allylidenetriphenylphosphorane reagent in the early stage of the synthetic strategy is advantageous for the rapid construction of highly functionalized key pyrrolo[1,2-& alpha;]azepine frameworks.

10aalkaloids10aBiomimetic synthesis10aClaisen rearrangement10acyclization10aRegioselectivity1 aChavan, Subhash, P.1 aKalbhor, Dinesh, B.1 aGonnade, Rajesh, G. uhttps://library.ncl.res.in/content/rapid-bioinspired-n-acyliminium-ion-strategy-abc-core-stemona-alkaloids