A General Entry to Antifeedant Sesterterpenoids: Total Synthesis of (+)‐Norleucosceptroid A, (−)‐Norleucosceptroid B, and (−)‐Leucosceptroid K1. (4th September 2014)

• Record Type: Journal Article
• Authors: Hugelshofer, Cedric L.; Magauer, Thomas
• Is Part Of: Angewandte Chemie. Volume 126:Number 42(2014)
• Page Start: 11533
• Page End: 11537
• Publication Date: 2014-09-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201407788
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The first asymmetric total synthesis of the antifeedant terpenoids (+)‐norleucosceptroid A, (−)‐norleucosceptroid B, and (−)‐leucosceptroid K has been accomplished. This highly concise synthetic route was guided by our efforts to develop a platform for the collective synthesis of a whole family of antifeedant natural products. The synthesis features a Hauser–Kraus‐type annulation followed by an unprecedented, highly efficient intramolecular dilactol aldol‐type condensation reaction to produce the 5, 6, 5 skeleton. The developed synthetic route proceeds for norleucosceptroid A and B in 16 steps (longest linear sequence) from known compounds.</p> </abstract>