Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.

The asymmetric synthesis of the key pyrrolidinone core, including a highly elaborated exocyclic carbon chain, of the γ-lactam β-lactone antibiotic oxazolomycin A is described. Principal features include the Birch reduction of an aromatic pyrrole nucleus, a late stage RuO(4) catalyzed pyrrolidine oxi...

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Main Authors: Donohoe, T, O'Riordan, T, Peifer, M, Jones, C, Miles, T
Format: Journal article
Language:English
Published: 2012
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author Donohoe, T
O'Riordan, T
Peifer, M
Jones, C
Miles, T
author_facet Donohoe, T
O'Riordan, T
Peifer, M
Jones, C
Miles, T
author_sort Donohoe, T
collection OXFORD
description The asymmetric synthesis of the key pyrrolidinone core, including a highly elaborated exocyclic carbon chain, of the γ-lactam β-lactone antibiotic oxazolomycin A is described. Principal features include the Birch reduction of an aromatic pyrrole nucleus, a late stage RuO(4) catalyzed pyrrolidine oxidation, and a highly diastereoselective organocerium addition to an aldehyde.
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spelling oxford-uuid:9b8c1c17-9e48-4f67-95ae-0912078fbaf32022-03-27T00:29:30ZAsymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:9b8c1c17-9e48-4f67-95ae-0912078fbaf3EnglishSymplectic Elements at Oxford2012Donohoe, TO'Riordan, TPeifer, MJones, CMiles, TThe asymmetric synthesis of the key pyrrolidinone core, including a highly elaborated exocyclic carbon chain, of the γ-lactam β-lactone antibiotic oxazolomycin A is described. Principal features include the Birch reduction of an aromatic pyrrole nucleus, a late stage RuO(4) catalyzed pyrrolidine oxidation, and a highly diastereoselective organocerium addition to an aldehyde.
spellingShingle Donohoe, T
O'Riordan, T
Peifer, M
Jones, C
Miles, T
Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.
title Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.
title_full Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.
title_fullStr Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.
title_full_unstemmed Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.
title_short Asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin A.
title_sort asymmetric synthesis of the fully elaborated pyrrolidinone core of oxazolomycin a
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AT milest asymmetricsynthesisofthefullyelaboratedpyrrolidinonecoreofoxazolomycina