Asymmetric, Protecting-Group-Free Total Synthesis of (+)-Caribenol A

Asymmetric, Protecting-Group-Free Total Synthesis of (+)-Caribenol A

Caribenol Queen: A new asymmetric, protecting‐group‐free synthesis of the marine tetracyclic diterpenoid (+)‐caribenol A (1) has been achieved. The enantioselective synthesis employed (S)‐methyl 1‐methyl‐2‐oxocyclopent‐3‐enecarboxylate as a chiral scaffold, and an intramolecular Diels–Alder (IMDA) r...

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Veröffentlicht in:Chemistry, an Asian journal an Asian journal, 2013-09, Vol.8 (9), p.1972-1975
Hauptverfasser: Han, Jing-Chun, Liu, Lian-Zhu, Li, Chuang-Chuang, Yang, Zhen
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric synthesis
Chemistry
Crystallography, X-Ray
Cycloaddition Reaction
Diels-Alder reaction
Diterpenes - chemical synthesis
Diterpenes - chemistry
Hydrogenation
intramolecular
Molecular Conformation
Stereoisomerism
synthetic methods
total synthesis
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Zusammenfassung:Caribenol Queen: A new asymmetric, protecting‐group‐free synthesis of the marine tetracyclic diterpenoid (+)‐caribenol A (1) has been achieved. The enantioselective synthesis employed (S)‐methyl 1‐methyl‐2‐oxocyclopent‐3‐enecarboxylate as a chiral scaffold, and an intramolecular Diels–Alder (IMDA) reaction of substrate 3 afforded the [5.7.6] tricyclic core in compound 2.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201300441