Synthesis of the Unusual Diterpenoid Tropones Hainanolidol and Harringtonolide

Frey, Barbara; Wells, Adam P.; Rogers, Daniel H.; Mander, Lewis N.

doi:10.1021/ja9738081

Cited by 109 publications

(51 citation statements)

References 13 publications

(11 reference statements)

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“…7). The diterpenoid tropones, hainanolidol and harringtonolide (hainanolide) were first isolated from seeds of Cephalotaxus harringtonia or the bark of the related Chinese species Cephalotaxus hainanensis (Taxaceae) [255,256,257]. Hainanolide was shown to be an inhibitor of plant growth in tobacco and beans.…”

Section: Diterpenoid Troponesmentioning

confidence: 99%

“…Due to the great promise for the use of these anticancer compounds in therapeutics, chemical synthesis was studied although with great challenges. Chemical synthesis of hainanolide and the structuraly close but biologically inactive carbinol, hainanolide, has been reported [257,259]. Two new lactones, fortunolides A and B together with hainanolidol were also isolated from the needles and stem of Cephalotaxus fortunei [260].…”

Section: Diterpenoid Troponesmentioning

confidence: 99%

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Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Zhao

2007

CMC

106

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Tropone or tropolone and its derivatives (here together called troponoids) belong to a family of natural products with a seven-membered aromatic ring and various side groups. They are mainly synthesized by plants and fungi, and most troponoids play roles of antibacterial defenses in these organisms. With an increasingly severe situation of antibiotic resistant bacteria, as well as a requirement for antifungal medicines, troponoids have attracted extensive studies since they have powerful antibacterial and antifungal activity, particularly against antibiotic-resistant bacteria. In addition, many other biological activities such as antiviral, antitumor, antioxidant, anti-inflammatory, insecticidal, or enzyme inhibitor activities are associated with troponoids. After extensive studies in the 1960s-70s, interests in natural troponoids dedclined. However, chemical and biomedical studies on troponoids bloom again from the 1990s. To date great progress has been made with troponoid study in terms of identification of new natural troponoids, chemical synthesis and properties, biological activity, biosynthesis and metabolism. Particularly, bioassay-guided screening strategy and structure-activity relation-directed structure modification and drug design has resulted in the synthesis and discovery of many new derivatives. Many of them have great promise to be developed into new medicines for their potent and specific activities. This review presents the recent advances in troponoid studies and highlights multiple faceted biological activities of troponoids, as well as their relationships with chemical structures. Chemistry, biosynthesis, and production via biotechnology of troponoids are also briefly reviewed. Applications of troponoids in daily life, agriculture, medicine, and industry, and the related patents have been considered to further extend our understanding of the increasing impact of troponoids on humans.

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Section: Diterpenoid Troponesmentioning

confidence: 99%

Section: Diterpenoid Troponesmentioning

confidence: 99%

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Zhao

2007

CMC

106

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“…[5] When the reaction leads to a highly strained five-six bicyclic system, the reaction usually follows a different path such as electrophilic aromatic substitution. [2] This type of reaction also finds applications in the synthesis of benzo-fused bicyclic systems.…”

mentioning

confidence: 99%

“…To more precisely determine the rate influences by the substituents, intermolecular competition experiments were carried out as Scheme 4. Transition-metal-free synthesis of [6,5,7]benzo-fused ring compounds. All reactions were performed with 3 a-u (0.40 mmol), NaH (0.48 mmol) in 4.0 mL toluene at 110 8C for 15 h. All the yields refer to isolated products.…”

mentioning

confidence: 99%

“…In summary, we have developed a simple and efficient method to access fluorenes and [6,5,7]benzo-fused rings through transition-metal-free intramolecular aromatic substitution/Büchner reaction, using N-tosylhydrazones as nonstabilized diazo compound precursors. A literature survey indicates that there are few synthetically useful methods for the construction of these structures.…”

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confidence: 99%

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Transition‐Metal‐Free Intramolecular Carbene Aromatic Substitution/Büchner Reaction: Synthesis of Fluorenes and [6,5,7]Benzo‐fused Rings

et al. 2015

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Intramolecular aromatic substitution and Büchner reaction have been established as powerful methods for the construction of polycyclic compounds. These reactions are traditionally catalyzed by Rh II catalysts with a-diazocarbonyl compounds as the substrates. Herein a transition-metal-free intramolecular aromatic substitution/Büchner reaction is presented. These reactions use readily available N-tosylhydrazones as the diazo compound precursors and show wide substrate scope.

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Large‐Ring Carbocycles

2010

Name Reactions for Carbocyclic Ring Formations

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Synthesis of the Unusual Diterpenoid Tropones Hainanolidol and Harringtonolide

Cited by 109 publications

References 13 publications

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Transition‐Metal‐Free Intramolecular Carbene Aromatic Substitution/Büchner Reaction: Synthesis of Fluorenes and [6,5,7]Benzo‐fused Rings

Large‐Ring Carbocycles

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