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Synfacts 2014; 10(12): 1233
DOI: 10.1055/s-0034-1379399
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Norleucosceptroids A, B, and K

Contributor(s):
Erick M. Carreira
,
Matthias Westphal
Hugelshofer CL, Magauer T * Ludwig-Maximilians-University Munich, Germany
A General Entry to Antifeedant Sesterterpenoids: Total Synthesis of (+)-Norleucosceptroid A, (–)-Norleucosceptroid B, and (–)-Leucosceptroid K.

Angew. Chem. Int. Ed. 2014;
53: 11351-11355
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Further Information

Publication History

Publication Date:
18 November 2014 (online)

 
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Key words

sesterterpenoids - antifeedants - leucosceptroids

Significance

The target compounds represent a family of sesterterpenoids with antifeedant activity against a variety of plant-feeding insects and pathogens. Their potential application in plant protection renders them highly interesting targets for total synthesis and biological profiling.


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Comment

The authors employed an interesting aldol-type condensation of dilactol F en route to G. H was subjected to a sequence including epoxidation followed by aluminum-mediated opening leading to the required syn-configured species I, which was elaborated into the unnatural enantiomers of norleucosceptoids A, B, and K.


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