Synthetic Studies toward Leucosceptroid Family of Natural Products

Leucosceptroids are sesterterpenoids with potent antifeedant and antifungal activities. In this paper, efforts on two synthetic strategies toward stereoselective total synthesis of the leucosceptroid family of natural products are reported. Intramolecular addition cyclization strategy could lead to...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 16; pp. 11040 - 11052
Main Authors Sun, Peng, Ao, Junli, Qiao, Tianjiao, Wu, Shuming, Liang, Guangxin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.08.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CORE
REAGENTS
ACYLATION
CANUM
CARBONYL-COMPOUNDS
NUCLEOPHILIC-ADDITION
GLANDULAR TRICHOMES
DIRECT OXIDATION
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Summary:Leucosceptroids are sesterterpenoids with potent antifeedant and antifungal activities. In this paper, efforts on two synthetic strategies toward stereoselective total synthesis of the leucosceptroid family of natural products are reported. Intramolecular addition cyclization strategy could lead to a stereochemically mismatched core structure, while intermolecular addition/ring-closing metathesis cyclization strategy successfully furnished an advanced common intermediate bearing eight contiguous stereogenic centers, including three tetra-substituted ones, which fully matches all the stereochemistry on the tricyclic framework in leucosceptroid H. Late-stage transformation of this intermediate to leucosceptroid H encountered difficulty in oxidizing the secondary hydroxyl group to a carbonyl group in the target. Instead of the desired oxidation, an interesting tricyclic spiral product originating from a C–C bond cleavage was observed.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02597