1-Phenyl-1H-naphtho-[1,2-e][1,3]oxazin-3(2H)-one.

In the title compound, C(18)H(13)NO(2), the naphthalene (r.m.s. deviation = 0.025 Å) and benzaldehyde (r.m.s. deviation = 0.006 Å) groups are oriented at a dihedral angle of 89.48 (4)°. The oxazine group is oriented at dihedral angles of 13.36 (4) and 85.08 (5)°, respectively, with respect to the naphthalene and benzaldehyde fragments. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(8) loops. The dimers are linked into [010] chains via N-H⋯O hydrogen bonds. Weak C-H⋯π links and aromatic π-π stacking between the centroids of the naphthalene phenyl rings [centroid-centroid separation = 3.5977 (8) Å] help to consolidate the packing.

Selected regiocontrolled transformations applied to the synthesis of (1S)-cis-chrysanthemic acid from (1S)-3,4-epoxy-2,2,5,5-tetramethylcyclohexanol.

(1S)-cis-Chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry using regiocontrolled epoxide ring opening, diol mono-oxidation and cyclopropanation.

Microbial transformations of gelomulide G: a member of the rare class of diterpene lactones.

Microbial transformation of gelomulide G (3beta,6beta-diacetoxy-8beta,14beta-epoxyabiet-13(15)-en-16,12-olide, 1) was carried out. Incubation of 1 with Aspergillus niger afforded two new metabolites, 3beta,6beta-diacetoxy-8beta,14beta-dihydroxyabiet-13(15)-en-16,12-olide (2) and 3beta,6beta-diacetoxy-14beta-hydroxyabieta-8(9),13(15)-dien-16,12-olide (3). While Cunninghamella elegans afforded the 14-epimer of 2, i.e., 3beta,6beta-diacetoxy-8beta,14alpha-dihydroxyabiet-13(15)-en-16,12-olide (4), along with 3beta-acetoxy-6beta-hydroxy-8beta,14beta-epoxyabiet-13(15)-en-16,12-olide (5). The structures of the transformed products 2-5 were deduced to be new on the basis of MS and NMR data.