Use of (+)-manool in the Synthesis of Natural Products. Part II. Diterpenes and Relatives

Salazar, Franklin; Villamizar, José

doi:10.3184/174751912x13563728953551

Cited by 15 publications

(7 citation statements)

References 58 publications

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“…23 γ-Bicyclohomofarnesal 19 and the bromide 20 were prepared by removing the side chain of the starting material 16 using a procedure reported by Villamizar et al [24][25] and used as key intermediaries in the preparation of derivatives 21a-23d. Compound 16 was oxidised according to a slightly modified method of Costa et al 26 that were tested, 22c, 23c and 23d presented good inhibition and, 23a and 23b inhibited the β-haematin formation as much as chloroquine (P > 0.05).…”

Section: Resultsmentioning

confidence: 99%

“…13-Benzyl-15,16-bisnorlabdanes 21a-23d were obtained from naturally occurring and commercially available (+)-manool 16, a labdane diterpene commonly used as semi-synthetic precursor for the synthesis of others labdane diterpenes. 23 γ-Bicyclohomofarnesal 19 and the bromide 20 were prepared by removing the side chain of the starting material 16 using a procedure reported by Villamizar et al [24][25] and used as key intermediaries in the preparation of derivatives 21a-23d.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Antimalarial and Antileishmanial Activity of Novel 13-Benzyl-15,16-Bisnorlabdane Derivatives

Salazar

Quintero

Domínguez

et al. 2013

Journal of Chemical Research

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Twelve 13-benzyl-15,16-bisnorlabdanes in which the C-13 and C-14 substituents are varied have been prepared from the naturally occurring labdane diterpene (+)-manool. These synthesised compounds were evaluated for antimalarial activity, in vitro as hemozoin formation inhibitors and in vivo against Plasmodium berghei. These derivatives were also assayed for antileishmanial activity against Leishmania mexicana. O CHO OHC 3 CHO R 4 R = CHO 5 R = CH(OC 2 H 5 ) 2

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis, Antimalarial and Antileishmanial Activity of Novel 13-Benzyl-15,16-Bisnorlabdane Derivatives

Salazar

Quintero

Domínguez

et al. 2013

Journal of Chemical Research

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“…The bicyclic terpenoid side chain has been obtained from available natural diterpenoids or by total synthesis in a racemic [ 132 , 133 ] or chiral form [ 134 , 135 ]. Examples of natural diterpenoids used as starting material for the three types of diterpenoid skeletons are kolavenic acid [ 136 ], ent -halimic acid available in big quantities from its natural sources [ 66 ], or manool, which is commercially available [ 137 ] ( Figure 32 ).…”

Section: Synthetic Approaches Towards the Natural Alkylpurines Andmentioning

confidence: 99%

Marine Alkylpurines: A Promising Group of Bioactive Marine Natural Products

et al. 2018

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Marine secondary metabolites with a purine motif in their structure are presented in this review. The alkylpurines are grouped according to the size of the alkyl substituents and their location on the purine ring. Aspects related to the marine source, chemical structure and biological properties are considered together with synthetic approaches towards the natural products and bioactive analogues. This review contributes to studies of structure–activity relationships for these metabolites and highlights the potential of the sea as a source of new lead compounds in diverse therapeutic fields.

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“…Reviews have been published on the aromatisation of terpenoids and steroids by dehydrogenation 1 and on the use of the readily available diterpenoid, manool in the synthesis of sesquiterpenoids and diterpenoids. 2,3 Research papers are grouped into those concerning monoterpenoids,sesquiterpenoids, diterpenoids and triterpenoids. The monoterpenoid camphor has been the source of many useful chiral auxiliaries and building blocks.…”

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Recent Advances in the Chemistry of the Terpenoids

Hanson

2015

Journal of Chemical Research

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Terpenoids are ubiquitous natural products that are characterised by a carbon skeleton which is assembled from isoprene units. Despite this common building block there are a wide range of structural types, many of which are chiral. They include compounds with a variety of biological activities. Consequently the terpenoids are of considerable interest in phytochemical, synthetic, biological and environmental research. Current studies include the elucidation of the structures of novel terpenoids particularly from plants that have been used in folk medicine. Since some terpenoids are readily available, their structures and in particular their chirality, make them useful starting materials for the synthesis of rarer natural products not only to confirm the structure of the latter but also to explore structure-biological activity relationships.Articles published in the Journal of Chemical Research between January 2012 and June 2015, exemplify a wide variety of studies in terpenoid natural product chemistry. Reviews have been published on the aromatisation of terpenoids and steroids by dehydrogenation 1 and on the use of the readily available diterpenoid, manool in the synthesis of sesquiterpenoids and diterpenoids. 2,3 Research papers are grouped into those concerning monoterpenoids,sesquiterpenoids, diterpenoids and triterpenoids. The monoterpenoid camphor has been the source of many useful chiral auxiliaries and building blocks. A new camphor-derived chiral auxiliary and its application to the asymmetric Darzens reaction has been reported 4 whilst an environmentally friendly preparation of 3-bromocamphor and camphorquinone has been described. 5 The role of endophytic micro-organisms and their metabolites in the ecological chemistry of their host plants is a subject of considerable interest. Novel sesquiterpenes with a tremulane carbon skeleton including ceriponol P, have been isolated 6,7 from the fungus Ceriporia lacerate which is an endophyte in Huperzia serrata, the clubmoss that is the source of the alkaloids huperzine A and B which are used for the treatment of age-related memory loss. Sesquiterpenoid lactones are characteristic of the Compositae (Asteraceae). A new guaianolide glycoside has been isolated 8 from the roots of Pterocypsela elata.Over 500 tetracyclic diterpenoids, many of which have tumour-inhibitory properties, have been obtained from Isodon (Lamiaceae) species. These plants are widely used in traditional Chinese medicines. Further examples of these diterpenoids have been reported from I. lophanthoides, 9 I. japonicus 10 and I. serra. 11 Readily available diterpenoids have been used as carriers for pharmacophores in the treatment of malaria 12 and cytotoxic components such as chlorambucil. 13 The synthesis of rosmic acid derivatives from the more readily available rosmanol and carnosol has been described 14 in the context of their biological activity. Andrographolide is a labdane whose biological activity as an anti-cancer agent is attracting some interest. An unexpected elimination reaction has ...

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Use of (+)-manool in the Synthesis of Natural Products. Part II. Diterpenes and Relatives

Abstract: The syntheses of several kind of natural product skeletal including as ring C aromatic diterpenes, labdane, diterpenoid, purines and tricarbocyclic diterpenes from the diterpenoid (+)-manool are described in this review.

Cited by 15 publications

References 58 publications

Synthesis, Antimalarial and Antileishmanial Activity of Novel 13-Benzyl-15,16-Bisnorlabdane Derivatives

Synthesis, Antimalarial and Antileishmanial Activity of Novel 13-Benzyl-15,16-Bisnorlabdane Derivatives

Marine Alkylpurines: A Promising Group of Bioactive Marine Natural Products

Recent Advances in the Chemistry of the Terpenoids

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