Skip to main content
. Author manuscript; available in PMC: 2019 Sep 22.
Published in final edited form as: Nat Chem. 2019 Mar 22;11(4):342–350. doi: 10.1038/s41557-019-0230-0

Figure 3. Pharmacophore-directed retrosynthesis applied to gracilin A:

Figure 3

a, Synthesis of a highly simplified analogue bearing the proposed pharmacophore. b, Assembly of the cis–fused, 6,5–bicyclic core 15a of gracilin A through an enantioselective, organocatalytic Diels–Alder/lactonization cascade and manipulation to a simplified bicyclic analog 7. c, Annulation of the natural and a simplified cyclohexyl moiety. (inset: ORTEP representation of the single crystal X-ray structure of (–)-21b)