Novel bibenzyl derivatives and ent-cuparene-type sesquiterpenoids from Radula species

Asakawa, Yoshinori; Takikawa, Keiko; Toyota, Masao; Takemoto, Tsunematsu

doi:10.1016/0031-9422(82)85245-x

Cited by 46 publications

(29 citation statements)

References 22 publications

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“…As an application of this methodology, radulanin A ( 4 a ) was synthesized after a challenging aromatization of the cyclohexenone ring on 13 . Based on an allelopathic hypothesis, radulanins were postulated as potential herbicides due to their structural analogy with the bibenzyl natural product lunularic acid ( 15 , Figure ) . In this study, the weed‐killing power of natural product 4 a is thus demonstrated.…”

Section: Introductionmentioning

confidence: 68%

One‐Pot Synthesis of Metastable 2,5‐Dihydrooxepines through Retro‐Claisen Rearrangements: Method and Applications

Zhang

Baudouin

Cordier

et al. 2019

Chemistry A European J

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A one‐pot methodology to synthesize metastable bicyclic 2,5‐dihydrooxepines from cyclic 1,3‐diketones and 1,4‐dibromo‐2‐butenes through the retro‐Claisen rearrangement of syn‐2‐vinylcyclopropyl diketone intermediates is reported. DFT calculations were performed to understand the reaction selectivity and mechanisms towards [1,3]‐ or [3,3]‐sigmatropic rearrangements, highlighting the crucial influence of the temperature. The reaction was successfully applied to a short protecting group‐free total synthesis of radulanin A, a natural 2,5‐dihydrobenzoxepine. Moreover, the strong herbicidal potential of this natural product is demonstrated for the first time.

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Section: Introductionmentioning

confidence: 68%

One‐Pot Synthesis of Metastable 2,5‐Dihydrooxepines through Retro‐Claisen Rearrangements: Method and Applications

Zhang

Baudouin

Cordier

et al. 2019

Chemistry A European J

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“…However, in Helichrysum umbraculigerum Less., a species from the family Compositae, the presence of CBGA, CBG and analogous to CBG was reported (Bohlmann and Hoffmann 1979). Moreover, in liverworts from Radula species the isolation of geranylated bibenzyls analogous to CBG was reported (Asakawa et al 1982), suggesting homology of PKS and prenylase genes from the cannabinoid pathway in other species. Crombie et al (1988) reported the chemical synthesis of bibenzyl cannabinoids.…”

Section: Resultsmentioning

confidence: 94%

Secondary metabolism in cannabis

2008

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Cannabis sativa L. is an annual dioecious plant from Central Asia. Cannabinoids, flavonoids, stilbenoids, terpenoids, alkaloids and lignans are some of the secondary metabolites present in C. sativa. Earlier reviews were focused on isolation and identification of more than 480 chemical compounds; this review deals with the biosynthesis of the secondary metabolites present in this plant. Cannabinoid biosynthesis and some closely related pathways that involve the same precursors are disscused.

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“…Radulanins H (1) 1 and E (2), 2 isolated by Asakawa et al from the liverwort Radula perrottetii and Radula variabilis, are 3-methyl-2,5-dihydro-1-benzoxepin derivatives 3 (Fig. 1).…”

Section: Introductionmentioning

confidence: 96%