Synthese stereoselective DU (±)-β-santalol

Performance evaluation of a versatile multidimensional chromatographic preparative system based on three-dimensional gas chromatography and liquid chromatography–two-dimensional gas chromatography for the collection of volatile constituents

“…Although several synthetic procedures have been exploited for the production of such components, these ways are not cost-effective and, hence, sandalwood essential oil remains the only viable source of these sesquiterpene alcohols [11][12][13][14][15][16]. The widespread used fractional distillation may be unrewarding procedure, since these components have the tendency to be distilled at the same temperature as a mixture [17].…”

Enantioselective Synthesis of (−)‐β‐Santalol by a Copper‐Catalyzed Enynol Cyclization–Fragmentation Reaction

“…[1] Despite extensive efforts, this excellent fragrance ingredient is still not commercially available.…”

“…[1] The key step in the synthesis is an efficient copper-catalyzed rearrangement of an enynol.The increasing scarcity of East Indian sandalwood oil [2] has motivated research chemists over the last 40 years to develop a synthesis of the most valuable component, (À)-b-santalol (À)-1, which makes up 20-25 % of the composition of the oil, or its racemate. [1] Despite extensive efforts, this excellent fragrance ingredient is still not commercially available.Recently, we reported the cost-efficient copper-catalyzed cycloisomerization of 5-en-1-yn-3-ols (cyclopropanation/1,2alkyl shift; Scheme 1, A!E) [3] and related enynol esters. [4] These cyclopropanation reactions, [5] which lead selectively to complex polycyclic compounds, are generally catalyzed by platinum [6] or gold.…”

“…We report herein the first enantioselective, direct synthesis of the highly prized natural sandalwood odorant (À)-b-santalol ((À)-1). [1] The key step in the synthesis is an efficient copper-catalyzed rearrangement of an enynol.…”

Hydrogenation towards Synthetic Sandalwood Odorants in Fragrance Industry

“…Despite the difficulty to evaluate the contribution of each constituent to sandalwood oil overall odor profile, (À )-(Z)-β-santalol, whose structure was first elucidated by Ružička in 1935, [9] is unanimously considered as the gold standard of the sandalwood odorants. Whereas there is still no synthetic quality on the market (optically active or racemic, the other enantiomer being odorless), access to (Z)-βsantalol has been attracting lot of attention [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] but with only few potentially industrially viable pathways. [24 -29] In the meantime, some important research has also been conducted on the discovery of easier ways to synthesize molecules displaying the desired sandalwood olfactive character.…”