Synthesis of sesquiterpenoids of the drimane group from labdane diterpenoids

Abstract

of Moldova. Fax." 007 (042 2) 73 9954Data on the partial synthesis of enantiomerically pure sesquiterpenoids of the drimane group, including valuable biologically active natural compounds, from accessible labdane diterpenoids are surveyed.

Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part I.

“…Oxidative cleavage reactions of the side chain of communic acids with ozone and the OsO 4 -NaIO 4 system have been reported previously [14]. The synthesis of sesquiterpenoids from labdane diterpenoids has also been reported [15]. On the other hand, degradations in the side chain of dihydrozamoranic acid were used for the synthesis of drimane [16].…”

1H and 13C NMR spectra of some drimanic sesquiterpenoids

“…1 The practi cally valuable properties of drimanes and their low con tents in natural sources stimulate works aimed at their synthesis. 2 This study is devoted to analysis of the 1 H and 13 C NMR spectra of a series of drimanic sesquiterpenoids using advanced multipulse NMR techniques, which al low unambiguous assignment of the chemical shifts of magnetic nuclei.…”

Synthesis of Drimanes from (+)-Larixol

“…The biological activities of some drimane sesquiterpenoids have greatly stimulated the development of new synthetic routes to this class of compounds, and many syntheses of drimanes have appeared in the last twenty years. [1][2][3] The oleoresin of larch (Larix decidua, L. europea) 4,5 contains large amounts of the labdane diterpene larixol 1 (>10 weight%), which can be easily isolated from larix turpentine in pure form. 5 In view of its availability and its chemical structure, larixol seems to be a suitable starting material for the synthesis of isoprenoids possessing a 4,4,10-trimethyldecalin skeleton.…”