Proof of the structure of the Stemodia chilensis tetracyclic diterpenoid (+)-19-acetoxystemodan-12-ol by synthesis from (+)-podocarpic acid. X‑ray structure determination of a key intermediate
| Autor: | Rinaldo Marini Bettolo, Doriano Lamba, Francesca Leonelli, Luisa Maria Migneco, Azzurra Mostarda, Luca De Angelis, Nicola Demitri, Francesca Ceccacci, Angela La Bella |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Synthesis
stemodane diterpenoid (+) podocarpic acid X-ray structure determination Stereochemistry Stemodia Molecular Conformation Pharmaceutical Science Stereoisomerism Microbial Sensitivity Tests 010402 general chemistry Crystallography X-Ray 01 natural sciences Molecular conformation Analytical Chemistry 19-acetoxystemodan-12-ol Podocarpic acid Drug Discovery Chile Nuclear Magnetic Resonance Biomolecular Pharmacology biology Calceolaria Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry X-ray Plantaginaceae biology.organism_classification Terpenoid 0104 chemical sciences Complementary and alternative medicine Abietanes Molecular Medicine Stemodia chilensis Diterpenes |
| Zdroj: | Journal of natural products 79 (2016): 1155–1159. doi:10.1021/acs.jnatprod.5b00834 info:cnr-pdr/source/autori:Leonelli F.; Mostarda A.; De Angelis L.; Lamba D.; Demitri N.; La Bella A.; Ceccacci F.; Migneco L.M.; Marini Bettolo R./titolo:Proof of the Structure of the Stemodia chilensis Tetracyclic Diterpenoid (+)-19-Acetoxystemodan-12-ol by Synthesis from (+)-Podocarpic Acid: X-ray Structure Determination of a Key Intermediate/doi:10.1021%2Facs.jnatprod.5b00834/rivista:Journal of natural products (Print)/anno:2016/pagina_da:1155/pagina_a:1159/intervallo_pagine:1155–1159/volume:79 |
| DOI: | 10.1021/acs.jnatprod.5b00834 |
| Popis: | The first synthesis of (+)-19-acetoxystemodan-12-ol (1), a stemodane diterpenoid isolated from Stemodia chilensis, is described. The structure was supported by an X-ray crystallographic analysis of intermediate (+)-9a, which confirmed the proposed structure and excluded the structure of (-)-19-hydroxystemod-12-ene as a possible candidate for the Chilean Calceolaria diterpenoid to which the (-)-19-hydroxystemar-13-ene structure (9b) had been erroneously assigned. |
| Databáze: | OpenAIRE |
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