Formal enantioselective synthesis of nhatrangin A.
| Title: | Formal enantioselective synthesis of nhatrangin A. |
|---|---|
| Authors: | Feuillastre S; Université de Lyon - Université Claude Bernard Lyon 1 - CNRS - INSA Lyon - CPE Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires - UMR 5246, équipe SURCOOF, Campus Lyon-Tech-La Doua, bât. Raulin, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France. beatrice.pelotier@univ-lyon1.fr piva@univ-lyon1.fr.; Raffier L; Université de Lyon - Université Claude Bernard Lyon 1 - CNRS - INSA Lyon - CPE Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires - UMR 5246, équipe SURCOOF, Campus Lyon-Tech-La Doua, bât. Raulin, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France. beatrice.pelotier@univ-lyon1.fr piva@univ-lyon1.fr.; Pelotier B; Université de Lyon - Université Claude Bernard Lyon 1 - CNRS - INSA Lyon - CPE Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires - UMR 5246, équipe SURCOOF, Campus Lyon-Tech-La Doua, bât. Raulin, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France. beatrice.pelotier@univ-lyon1.fr piva@univ-lyon1.fr.; Piva O; Université de Lyon - Université Claude Bernard Lyon 1 - CNRS - INSA Lyon - CPE Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires - UMR 5246, équipe SURCOOF, Campus Lyon-Tech-La Doua, bât. Raulin, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France. beatrice.pelotier@univ-lyon1.fr piva@univ-lyon1.fr. |
| Source: | Organic & biomolecular chemistry [Org Biomol Chem] 2020 Mar 11; Vol. 18 (10), pp. 1949-1956. |
| Publication Type: | Journal Article; Research Support, Non-U.S. Gov't |
| Language: | English |
| Journal Info: | Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101154995 Publication Model: Print Cited Medium: Internet ISSN: 1477-0539 (Electronic) Linking ISSN: 14770520 NLM ISO Abbreviation: Org Biomol Chem Subsets: MEDLINE; PubMed not MEDLINE |
| Imprint Name(s): | Original Publication: Cambridge, UK : Royal Society of Chemistry, c2003- |
| Abstract: | A new and straightforward synthesis of the C1-C7 core fragment of nhatrangin A was achieved in 14 steps from achiral 3-hydroxybenzaldehyde, without the need of chiral reagents or enzymatic resolution to introduce the chiral centers. The key asymmetric steps include in particular a highly enantioselective organocatalyzed Michael addition on an aryl vinyl ketone, a Sharpless asymmetric epoxidation and a subsequent regioselective ring opening of the resulting chiral epoxide. This work represents the first formal enantioselective synthesis of nhatrangin A. |
| Entry Date(s): | Date Created: 20200227 Date Completed: 20200320 Latest Revision: 20200320 |
| Update Code: | 20260130 |
| DOI: | 10.1039/c9ob02639h |
| PMID: | 32101216 |
| Database: | MEDLINE |
Journal Article; Research Support, Non-U.S. Gov't