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Synfacts 2018; 14(04): 0333
DOI: 10.1055/s-0037-1609334
DOI: 10.1055/s-0037-1609334
Synthesis of Natural Products and Potential Drugs
Syntheses of Plakortin Polyketides
Li Q.
Zhao K.
Peuronen A.
Rissanen K.
Enders D.
*
Tang Y.
* Tsinghua University, Beijing and Sichuan University, Chengdu, P. R. of China; RWTH Aachen University, Germany; University of Jyväskylä, Finland
Enantioselective Total Syntheses of (+)-Hippolachnin A, (+)-Gracilioether A, (–)-Gracilioether E, and (–)-Gracilioether F.
J. Am. Chem. Soc. 2018;
140: 1937-1944
Enantioselective Total Syntheses of (+)-Hippolachnin A, (+)-Gracilioether A, (–)-Gracilioether E, and (–)-Gracilioether F.
J. Am. Chem. Soc. 2018;
140: 1937-1944
Further Information
Publication History
Publication Date:
15 March 2018 (online)
Key words
Plakortin polyketides - (+)-hippolachnin A - gracilioethers - organocatalysis - [2+2] photocycloaddition - HAT-triggered oxygenation
Significance
(+)-Hippolachnin A and the gracilioethers commonly feature a strained, bowl-shaped tricyclic core. Based on a [2+2]-photocycloaddition strategy, the authors report divergent syntheses of four different Plakortin natural products.
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Comment
An organocatalytic, asymmetric 1,4-addition afforded γ-butenolide D, which served as a common intermediate. Chain elongation gave ester G, which after desaturation and [2+2] photocycloaddition, yielded (+)-hippolachnin A.
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