Synthesis of biologically active drimanes and homodrimanes from (−)-sclareol

Optically Active Ionones and Derivatives: Preparation and Olfactory Properties

“…However, a reduction procedure [58] employing Bu 3 SnH and catalytic amounts of (PPh 3 In 2000, Barrero et al [59] reported a synthesis of dihydro-γ-ionone [(ϩ)-7] from (Ϫ)-sclareol. The latter compound was converted into 56, [60] which was then subjected to a Grob fragmentation to provide the seco-sesquiterpene 57. [61] Thermal rearrangement of the ozonide of 57 furnished a mixture of formate 58 and dihydro-γ-ionone (ϩ)-7, but no data on the optical purity were provided.…”

Selective Isomerization of Epoxides to Allylic Alcohols Catalyzed by TiO2‐Supported Gold Nanoparticles

“…We emphasize that in several cases (products 5 a, [16] 11 a, [17] and 12 a [18] ) the regioselectivity for allylic alcohol formation is exceptional. Therefore, the new double bond is always formed with hydrogen atom abstraction from the least hindered position.…”

Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol

“…4,12,13 The treatment of the acetyl derivative 13 with Na 2 CrO 4 and NaOAc in AcOH gave 14 in a high yield (Scheme 2). The 8-en-7-one group of 14 is suitable for transforming into the 7-en-9-ol functionality of warburganal (4). This can be achieved by two alternative procedures: via Wharton rearrangement of the ketoepoxyde 15 or through allylic isomerization of the mesylate derived from 17.…”

“…The great variety and strength of the biological activities 1 of these compounds have greatly stimulated the development of general synthetic routes for them. 2 Following the authors' research on the synthesis of bioactive drimanes from (-)-sclareol (1) 3,4 and (-)-drimenol (6), [5][6][7][8] active compounds 2 and 4 have been prepared. 11,12-Epoxydrim-8,12-en-11-ol (2) was isolated by Capon et al from a marine sponge of the genus Dysidea, 9 but these authors were unable to fully characterize this drimane due to its considerable instability.…”