Iodo-cyclizations: Novel Strategy for the Total Syntheses of Polyrhacitide A and epi-Cryptocaryolone

Highly stereoselective total syntheses of polyrhacitide A and epi-cryptocaryolone have been achieved in 11 steps with high overall yield of 24% and 28%, respectively, following a recently developed strategy for the construction of trans-2,6-disubstituted-3,4-dihydropyrans. In this report, the versat...

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Bibliographic Details
Published in:Organic letters 2011-02, Vol.13 (4), p.744-747
Main Authors: Mohapatra, Debendra K, Bhimireddy, Eswar, Krishnarao, P. Sivarama, Das, Pragna P, Yadav, J. S
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Cyclization
Iodine - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Pyrones - chemical synthesis
Pyrones - chemistry
Stereoisomerism
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Summary:Highly stereoselective total syntheses of polyrhacitide A and epi-cryptocaryolone have been achieved in 11 steps with high overall yield of 24% and 28%, respectively, following a recently developed strategy for the construction of trans-2,6-disubstituted-3,4-dihydropyrans. In this report, the versatility of iodo-cyclization for the total syntheses of polyrhacitide A and epi-cryptocaryolone is demonstrated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1029854