Synfacts 2018; 14(07): 0663
DOI: 10.1055/s-0037-1609866
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Divergent Approach to Enmein-Type Natural Products

Erick M. Carreira
Niels Sievertsen
Pan S. Chen S. Dong G. * University of Chicago and University of Texas at Austin, USA
Divergent Total Syntheses of Enmein-Type Natural Products: (–)-Enmein, (–)-Isodocarpin, and (–)-Sculponin R.

Angew. Chem. Int. Ed. 2018;
57: 6333-6336
Further Information

Publication History

Publication Date:
18 June 2018 (online)



Dong and co-workers have attained three highly oxygenated ent-kaurenoids from the isodon family of natural products by means of total synthesis. The significance of the work lies in the expeditious construction of key intermediate L, which was subsequently utilized as a common starting point in the preparation of (–)-sculponin R, (–)-isodocarpin, and (–)-enmein.



The authors commenced their synthetic route with the assembly of bicyclic ketone E by Diels–Alder cycloaddition. Birch reduction provided access to acetal G, which was subsequently transformed into enone I. In a single pot, Dong and co-workers constructed pivotal vinyl bromide L. Relying on reductive alkenylation strategies, this penta­cycle was used to access the three highlighted natural products.