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Synlett 1996; 1996(4): 391-392
DOI: 10.1055/s-1996-5405
DOI: 10.1055/s-1996-5405
letter
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Preparation of 3-Butadienyl Tetrahydrofurans and α-Butadienyl γ-Butyrolactones by Radical Cyclization of β-Bromopent-4-en-2-ynyl Ethers and mixed Acetals
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Publication History
Publication Date:
31 December 2000 (online)
SmI2- or Bu3SnH-promoted radical carbocyclization of β-bromopent-4-en-2-ynyl ethers 1a-e and of the corresponding mixed acetals 3a,b,d,e respectively affords 3-butadienyl tetrahydrofurans 2a-e and 4a,b,d,e, which are precursors of α-butadienyl γ-butyrolactones 5a,b,d,e by oxidation.
Radical carbocyclization - SmI2 - β-bromopropargyl ethers - 3-butadienyl tetrahydrofurans - α-butadienyl γ-butyrolactones