Synfacts 2025; 21(07): 665
DOI: 10.1055/a-2601-4755
Synthesis of Natural Products

Total Synthesis of (–)-Colombiasin A

Contributor(s):
,
Sebastian Kölbl
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
 

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.


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.




Publication History

Article published online:
23 June 2025

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