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Synfacts 2016; 12(05): 0441
DOI: 10.1055/s-0035-1562026
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Hippolachnin A

Contributor(s):
Erick M. Carreira
,
Leonardo J. Nannini
McCallum ME, Rasik CM, Wood JL, * Brown MK. * Baylor University, Waco and Indiana University, Bloomington, USA
Collaborative Total Synthesis: Routes to (±)-Hippolachnin A Enabled by Quadricyclane Cycloaddition and Late-Stage C–H Oxidation.

J. Am. Chem. Soc. 2016;
138: 2437-2442
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Publication History

Publication Date:
18 April 2016 (online)

 
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Key words

collaborative total synthesis - quadricyclane [2+2] cycloaddition - (±)-hippolachnin - C–H oxidation

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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