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

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

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-hydro...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2016-04, Vol.79 (4), p.1155-1159
Hauptverfasser: Leonelli, Francesca, Mostarda, Azzurra, De Angelis, Luca, Lamba, Doriano, Demitri, Nicola, La Bella, Angela, Ceccacci, Francesca, Migneco, Luisa M, Marini Bettolo, Rinaldo
Format: Artikel
Sprache:eng
Schlagworte:
Chile
Crystallography, X-Ray
Diterpenes
Diterpenes, Abietane - chemistry
Microbial Sensitivity Tests
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plantaginaceae - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.5b00834