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Issue 11, 2011
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Free radical 5-exo-dig cyclization as the key step in the synthesis of bis-butyrolactone natural products: experimental and theoretical studies

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Abstract

Radical cyclization reactions were performed by 5-exo-dig mode to yield cis-fused bicyclic systems, leading to the synthesis of bis-butyrolactone class of natural products. The study was aimed at understanding the impact of alkyl side chains of furanoside ring systems in L-ara configuration on the radical cyclization. It was amply demonstrated by experimental studies that the increase in the length of the alkyl side chain has an effect on the cyclization: while efficient cyclization reactions could be realized with methyl and ethyl side chains, the yields were significantly reduced in the case of n-pentyl side chain. Theoretical studies using DFT and (RO)MP2 methods were carried out to analyze the influence of the substitution pattern on the cyclization barriers.

Graphical abstract: Free radical 5-exo-dig cyclization as the key step in the synthesis of bis-butyrolactone natural products: experimental and theoretical studies

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Publication details

The article was received on 05 Jan 2011, accepted on 05 Apr 2011 and first published on 06 Apr 2011


Article type: Paper
DOI: 10.1039/C1OB00019E
Org. Biomol. Chem., 2011,9, 4079-4084

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    Free radical 5-exo-dig cyclization as the key step in the synthesis of bis-butyrolactone natural products: experimental and theoretical studies

    G. V. M. Sharma, D. H. Chary, N. Chandramouli, F. Achrainer, S. Patrudu and H. Zipse, Org. Biomol. Chem., 2011, 9, 4079
    DOI: 10.1039/C1OB00019E

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