Synthesis of Drimanes from (+)-Larixol

Abstract

The selective transformation of the side chain of larixol 1 to a functionalized one-carbon moiety leads to 6,8-diacetoxydrimenal 13, which was converted to the drimanes (-)-albrassitriol (2), (-)-drimenol (3), (-)-uvidin C (4) and (-)-epi-albrassitriol (5).

Convenient synthesis of drimenol and its oxidation with selenium dioxide

“…1,8,9 This communication describes a simple and an effi cient synthesis of drimenol 1 from readily available drimane 8α,11 diol 11 monoacetate (3), which we ob tained previously 10 in a quantitative yield by peroxide oxidation of 8α hydroxy 11 bishomodriman 12 one (4). This terpenol has repeatedly served as a starting compound in the synthesis of diverse natural drimanes including those possessing biological ac tivities.…”

1,3-Cyclohexadien-1-Als: Synthesis, Reactivity and Bioactivities

“…The synthesis of (−)-drimenol has also been achieved by means of a reduction reaction of the corresponding cyclohexadiene carboxaldehyde derivative ( Scheme 51 ) [ 80 ]. Such reduction reaction unexpectedly involved the whole α,β-γ,δ-unsaturated aldehyde system.…”

“…Among them, reduction of the aldehyde moiety in the cyclohexadienal core is performed with NaBH4 in the presence of CeCl3 (Scheme 50). The synthesis of (−)-drimenol has also been achieved by means of a reduction reaction of the corresponding cyclohexadiene carboxaldehyde derivative (Scheme 51) [80]. Such reduction reaction unexpectedly involved the whole α,β-γ,δ-unsaturated aldehyde system.…”

Drimenol: A Versatile Synthon for Compounds with trans-Drimane Skeleton

“…The methodology developed for sclareol (2) has been successfully applied in the case of larixol [7] ( Figure 4). ii.…”

“…The methodology developed for sclareol (2) has been successfully applied in the case of larixol [7] (Figure 4). The semisynthesis of (-)-drimenol has also, been achieved from (+)-ambreinolide (7) [8], obtained, in turn, from manool [9,10].…”