Chemical methods for the synthesis and modification of neoclerodane diterpenes
Graphical abstract
Section snippets
Acknowledgements
The authors would like to thank the National Institute of Health and the National Institute on Drug Abuse, as well as the Universities of Iowa and Kansas for financial support of our ongoing research efforts. A.L. is currently supported by NIDA grant DA018151S1.
References and notes (62)
- et al.
Trends Plant Sci.
(2001) - et al.
J. Biol. Chem.
(1995) - et al.
J. Biol. Chem.
(1995) - et al.
Food Chem. Toxicol.
(2002) - et al.
Phytochemistry
(1986) - et al.
Cancer Lett.
(2002) - et al.
J. Ethnopharmacol.
(1983) J. Ethnopharmacol.
(1994)Life Sci.
(2005)- et al.
Bioorg. Med. Chem. Lett.
(2004)
Bioorg. Med. Chem. Lett.
Bioorg. Med. Chem. Lett.
Phytochemistry
Bioorg. Med. Chem. Lett.
Bioorg. Med. Chem. Lett.
Bioorg. Med. Chem. Lett.
Bioorg. Med. Chem. Lett.
Tetrahedron Lett.
Tetrahedron Lett.
Experientia
Nat. Prod. Rep.
Cell. Mol. Life Sci.
Int. Symp. Princess Takamatsu Cancer Res. Fund
Synthesis
J. Chem. Soc.
J. Antibiot.
J. Antibiot.
J. Agric. Food. Chem.
Phytother. Res.
J. Agric. Food. Chem.
Chem. Biodivers.
Cited by (17)
In vitro anti-trypanosomal potential of kaurane and pimarane semi-synthetic derivatives
2022, Natural Product ResearchLipid lowering agents of natural origin: An account of some promising chemotypes
2017, European Journal of Medicinal ChemistryCitation Excerpt :Additionally, it ameliorated obesity, impaired glucose tolerance, weight gain and other lipid parameters in obese C57BL/6 mice [240]. Although several approaches have been reported for the synthesis of clerodane and related diterpenes [241–243], but only three describe the synthesis of 40. Hagiwara et al. (1995) described the first total synthesis of 40 starting from an enantiomerically pure decalone [244].
From local to global - Fifty years of research on Salvia divinorum
2014, Journal of EthnopharmacologyCitation Excerpt :It is the diterpene salvinorin A that is responsible for the bioactivity in Salvia divinorum and which are also considered to be potential lead compounds in pharmaceutical research. Clerodanes are a structural class of diterpenes, which contain four contiguous stereo-centers contained in a cis or trans decalin (Lozama and Prisinzano, 2009). Neoclerodane diterpenes, a term originally coined in 1979 (Hanson, 2010), are a subtype of clerodanes, which have a carbon skeleton with the same absolute sterochemistry as clerodin, a bitter principle originally extracted from Clerodendron infortunatum Bhat. (
Semisynthetic neoclerodanes as kappa opioid receptor probes
2012, Bioorganic and Medicinal ChemistryCitation Excerpt :It was envisioned that this alteration would further investigate the amount of structural flexibility tolerated at the binding site of KOP receptors for neoclerodanes. Inversion of this center is synthetically challenging as 1 is a highly functionalized neoclerodane diterpene and has shown sensitivity to both acids and bases,31 however, 3 was synthesized by Béguin et al. in several steps and 19% overall yield.32 NMR and independent X-ray crystallographic data (see Supplementary data) were consistent with the previous report.
Biologically Active Diterpenoids in the Clerodendrum Genus—A Review
2022, International Journal of Molecular SciencesTotal syntheses of clerodane diterpenoids-A review
2019, Natural Product Communications