Total synthesis of (+)-laurencin: an asymmetric alkylation-ring-closing metathesis approach to medium ring ethers.
[formula: see text] The enantioselective total synthesis of (+)-laurencin 1 is achieved in 18 steps from (S)-(+)-4-benzyl-3-benzyloxyacetyl-2-oxazolidinone. The key steps in this synthesis are an asymmetric glycolate alkylation leading to acyl oxazolidinone 2 and a subsequent ring-closing olefin metathesis to construct the oxocene core of 1. The approach to medium ring ethers utilized in this synthesis provides a general and efficient route to the cyclic core of other marine natural products.
Crimmins
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Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill 27599-3290, USA. crimmins@email.unc.edu
Emmitte
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D000447:Aldehydes; D000478:Alkylation; D004987:Ethers; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000138:chemical synthesis*; D023303:Oxazolidinones; D035964:Oxocins; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
C410436:4-benzyl-3-benzyloxyacetyl-2-oxazolidinone; D000447:Aldehydes; D004987:Ethers; D004988:Ethers, Cyclic; D010080:Oxazoles; D023303:Oxazolidinones; D035964:Oxocins; C017460:laurencin