Six-Step Syntheses of (−)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N‑Z‑O‑TBDPS‑l‑serinal
Highly stereoselective six-step syntheses of (−)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by...
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| Published in | Journal of organic chemistry Vol. 81; no. 21; pp. 10569 - 10575 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
04.11.2016
Amer Chemical Soc |
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| Abstract | Highly stereoselective six-step syntheses of (−)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by Luche reduction and dihydroxylation (for altro-DNJ). The same sequence employing an epoxidation/epoxide opening in place of dihydroxylation furnishes manno-DNJ. |
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| AbstractList | Highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by Luche reduction and dihydroxylation (for altro-DNJ). The same sequence employing an epoxidation/epoxide opening in place of dihydroxylation furnishes manno-DNJ. Highly stereoselective six-step syntheses of (−)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by Luche reduction and dihydroxylation (for altro-DNJ). The same sequence employing an epoxidation/epoxide opening in place of dihydroxylation furnishes manno-DNJ. |
| Author | Garambel-Vilca, Edson Santiago, João V Talero, Alexánder G Burtoloso, Antonio C. B Rosset, Isac G Kawamura, Meire Y |
| AuthorAffiliation | Instituto de Química de São Carlos Universidade de São Paulo |
| AuthorAffiliation_xml | – name: Universidade de São Paulo – name: Instituto de Química de São Carlos |
| Author_xml | – sequence: 1 givenname: Meire Y surname: Kawamura fullname: Kawamura, Meire Y – sequence: 2 givenname: Alexánder G surname: Talero fullname: Talero, Alexánder G – sequence: 3 givenname: João V surname: Santiago fullname: Santiago, João V – sequence: 4 givenname: Edson surname: Garambel-Vilca fullname: Garambel-Vilca, Edson – sequence: 5 givenname: Isac G surname: Rosset fullname: Rosset, Isac G – sequence: 6 givenname: Antonio C. B surname: Burtoloso fullname: Burtoloso, Antonio C. B email: antonio@iqsc.usp.br |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27501028$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1002_cjoc_202000634 crossref_primary_10_1016_j_ccr_2017_09_003 crossref_primary_10_1021_acs_joc_1c03045 crossref_primary_10_1021_acs_orglett_6b03143 crossref_primary_10_1039_D3OB01624B crossref_primary_10_1002_adsc_201900450 crossref_primary_10_1002_ejoc_201800239 crossref_primary_10_5059_yukigoseikyokaishi_80_103 crossref_primary_10_1002_ejoc_202200636 |
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| Keywords | 1-DEOXYALTRONOJIRIMYCIN ACID-DERIVATIVES ASYMMETRIC-SYNTHESIS 1-DEOXYNOJIRIMYCIN NATURAL OCCURRENCE STEREOSELECTIVE-SYNTHESIS INDOLIZIDINES PIPERIDINES H INSERTION REACTIONS ALPHA,BETA-UNSATURATED DIAZOKETONES |
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| Snippet | Highly stereoselective six-step syntheses of (−)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are... Highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-L-serinal are... Highly stereoselective six-step syntheses of (-)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are... |
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| Title | Six-Step Syntheses of (−)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N‑Z‑O‑TBDPS‑l‑serinal |
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