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Synfacts 2016; 12(05): 0441
DOI: 10.1055/s-0035-1562026
DOI: 10.1055/s-0035-1562026
Synthesis of Natural Products and Potential Drugs
Synthesis of (±)-Hippolachnin A
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. April 2016 (online)
Key words
collaborative total synthesis - quadricyclane [2+2] cycloaddition - (±)-hippolachnin - C–H oxidation![](https://www.thieme-connect.de/media/synfacts/201605/i_c016_s1_10-1055_s-0035-1562026.gif)
Significance
In this work, the authors combine their independently elaborated routes into a unique collaborative total synthesis of (±)-hippolachnin A. The convergent synthesis relies on a [2+2] quadricyclane cycloaddition, followed by ring-opening metathesis and allylic C–H oxidation.
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Comment
Thermal [2+2] cycloaddition of acyl chloride A and quadricyclane B generated cyclobutane C after treatment with sodium hydroxide in moderate yield and excellent diastereoselectivity. Ring-opening metathesis catalyzed by Grubbs I under an ethylene atmosphere gave carboxylic acid D. A late stage C–H oxidation of bicycle D gave lactone F, which was converted in three further steps into (±)-hippolachnin A.
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![](https://www.thieme-connect.de/media/synfacts/201605/i_c016_s1_10-1055_s-0035-1562026.gif)