Two new neoclerodane diterpenoids, 6-deacetyl-teucrolivin A (5) and 8beta-hydroxy-teucrolivin B (6), were isolated from the aerial parts of Teucrium orientale, along with four already known neoclerodane diterpenoids, teucrolivin A (1), teucrolivin B (2), teucrolivin C (3) and teucrolivin H (4), previously isolated from Teucrium oliverianum. Their structures were elucidated on the basis of spectroscopic evidence and chemical transformations. Compounds 1-3 were assayed for antifeedant activity against Spodoptera littoralis, S. frugiperda and Heliocoverpa armigera. Teucrolivin A was the most potent of the three compounds tested.
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http://dx.doi.org/10.1248/cpb.52.1497 | DOI Listing |
Chem Commun (Camb)
June 2007
Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Ontario, CanadaK1N 6N5.
Tandem reactions have emerged as powerful strategies to synthesize complex structures, in particular, processes involving pericyclic reactions. This article describes recent advancement by our group in the development of novel tandem pericyclic reactions aimed at constructing diterpene frameworks.
View Article and Find Full Text PDFJ Org Chem
March 2006
Department of Chemistry, 10 Marie-Curie, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5.
Herein, we describe the synthesis of advanced intermediate 39 on the path towards the total synthesis of teucrolivin A (3) in 16 steps from commercially available 1,3-cyclohexadiene. We have constructed the trans-decalin core of the natural product 3 as a single diastereomer using a tandem oxy-Cope/Claisen/ene cascade and in doing so have incorporated sufficient functionality to allow completion of the total synthesis.
View Article and Find Full Text PDFChem Pharm Bull (Tokyo)
December 2004
Dipartimento di Chimica Organica E. Paternò, Università di Palermo, Viale delle Scienze, Parco d'Orleans II, Palermo, Italy.
Two new neoclerodane diterpenoids, 6-deacetyl-teucrolivin A (5) and 8beta-hydroxy-teucrolivin B (6), were isolated from the aerial parts of Teucrium orientale, along with four already known neoclerodane diterpenoids, teucrolivin A (1), teucrolivin B (2), teucrolivin C (3) and teucrolivin H (4), previously isolated from Teucrium oliverianum. Their structures were elucidated on the basis of spectroscopic evidence and chemical transformations. Compounds 1-3 were assayed for antifeedant activity against Spodoptera littoralis, S.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!