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Enantioselective, Organocatalytic Strategy for the Oxazolomycin Core: Formal Synthesis of (+)-Neooxazolomycin.
- Source :
-
Organic letters [Org Lett] 2020 Dec 04; Vol. 22 (23), pp. 9282-9286. Date of Electronic Publication: 2020 Nov 23. - Publication Year :
- 2020
-
Abstract
- A concise, organocatalytic, enantioselective route to the γ-lactam core of the oxazolomycins was developed. Key steps include a Lewis base-catalyzed, Michael proton transfer-lactamization organocascade, a one-pot N-methylation and diastereoselective α-alkylation, a diastereotopic group-selective reduction, a substrate-directed allylic hydroxylation, and a lanthanide-mediated organolithium addition to append the side chain. A formal synthesis of (+)-neooxazolomycin via interception of a Kende intermediate, accessed in 10 steps (previously 24 steps from α-d-glucose), enabled confirmation of the relative and absolute stereochemistry.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 22
- Issue :
- 23
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 33226820
- Full Text :
- https://doi.org/10.1021/acs.orglett.0c03511