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Synfacts 2025; 21(07): 665
DOI: 10.1055/a-2601-4755
DOI: 10.1055/a-2601-4755
Synthesis of Natural Products
Total Synthesis of (–)-Colombiasin A
Boezio AA,
Jarvo ER,
Lawrence BM,
Jacobsen EN *.
Harvard University, Cambridge, USA
Efficient Total Syntheses of (–)-Colombiasin A and (−)-Elisapterosin B: Application of the Cr-Catalyzed Asymmetric Quinone Diels–Alder Reaction.
Angew. Chem. Int. Ed. 2005;
44: 6046-6050
DOI: 10.1002/anie.200502178
Efficient Total Syntheses of (–)-Colombiasin A and (−)-Elisapterosin B: Application of the Cr-Catalyzed Asymmetric Quinone Diels–Alder Reaction.
Angew. Chem. Int. Ed. 2005;
44: 6046-6050
DOI: 10.1002/anie.200502178
Keywords
(–)-colombiasin A - marine diterpenoids - enantioselective hetero-Diels–Alder reaction - Negishi coupling - Wittig reaction - intermolecular Diels–Alder reaction - cross-metathesis - intramolecular Diels–Alder reaction - Barton–McCombie deoxygenation
Significance
In 2005, Jacobsen and co-workers reported the total synthesis of (–)-colombiasin A. Their synthetic strategy hinges on the employment of three sequential Diels–Alder reactions.
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Comment
The intramolecular Diels–Alder reaction was performed by elimination of the alcohol in quinone N, forming the diene in situ. Reduction and demethylation of O yielded the natural product.
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Publication History
Article published online:
23 June 2025
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