Vibsatin A is a new neurotrophic vibsane-type diterpenoid comprising bridged bicyclo[4.2.1]nonane skeleton. Inspired by Sawamura’s works, we generated the bicyclic backbone through Conia-ene-derived 7-exo-dig cyclization from an enantiomerically enriched TIPS-based silyl enol ether. The reaction, catalyzed sensitive gold(I) complex, was efficiently performed on large scale glovebox free techniq...

Clinical and experimental studies have consistently incriminated the medicinal plant germander (Teucrium chamaedrys L.) in epidemic and sporadic cases of liver diseases. The sacaca (Croton cajucara Benth), a common plant in Brazilian Amazon region also comes being incriminated in similar clinical cases. Of both plants were isolated diterpenoid coumpounds with similar chemical structures. Key-wo...

Covering: 2000 to 2008. Previous review: D. L. Wright and C. R. Whitehead, Org. Prep. Proced. Int., 2000, 32, 309-330. An overview of synthetic efforts toward cyathane diterpenoid natural products from the year 2000 to present is provided. The emphasis of this review is the various ring-constructing and stereoforming strategies employed in these synthetic routes.

In the title mol-ecule, C(20)H(26)O(3), a clerodane diterpenoid isolated from Dodonaea viscosa-, the trans-fused six-membered rings of the deca-line system display chair conformations. The five-membered lactone ring adopts an envelope conformation and the five-membered furan ring is essentially planar with a maximum deviation of 0.0052 (12) Å.

The relative stereochemistry of 3,4-secoisopimara-4(18),7,15-triene-3-oic acid, a diterpenoid with antispasmodic, hypotensive and antibacterial activities isolated from Salvia cinnabarina, was determined by an X-ray diffraction analysis of a single crystal of a suitable crystalline derivative.

Results of density functional theory calculations on possible mechanisms for formation of the diterpenoid cyclooctatin are described. These results are consistent with the involvement of an unexpected 1,3-alkyl shift that interconverts two cyclopropylcarbinyl carbocations and interchanges the positions of two carbon atoms in an 8-membered ring. Predictions for future experiments to provide furt...