77-42-9Relevant articles and documents
Hayashi et al.
, p. 1824,1825 (1965)
The synthesis of (Z)-trisubstituted allylic alcohols by the selective 1,4-hydrogenation of dienol esters: Improved synthesis of (-)-β-santalol
Fehr, Charles,Magpantay, Iris,Vuagnoux, Magali,Dupau, Philippe
experimental part, p. 1257 - 1260 (2011/04/16)
(E)-Trisubstituted allylic alcohols are commonly prepared from the corresponding (E)-enals, themselves readily accessible by a simple aldol condensation reaction. We demonstrate that these very same (E)-enals can be converted into (Z)-trisubstituted allylic acetates (and thus alcohols) by a ruthenium-catalyzed 1,4-hydrogenation of the corresponding dienol acetates. This simple solution to a long-lasting problem was applied to an industrially feasible synthesis of (-)-β-santalol.
Total Syntheses, Optical Rotations and Fragrance Properties of Sandalwood Constituents: (-)-(Z)- and (-)-(E)-β-Santalol and Their Enantiomers, ent-β-Santalene
Krotz, Achim,Helmchen, Guenter
, p. 601 - 610 (2007/10/02)
Enantiomerically pure 5-norbornene-2-carboxylic acids 4, obtained by asymmetric Diels-Alder additions, were oxidatively degraded to (+)- and (-)-2-norbornanone and (+)- and (-)-3-methyl-2-norbornanone which were converted into the title compounds by stereoselective alkylations, subsequent cis- and trans-selective Wittig reactions and reductions.Precise optical rotations were determined for (Z)- and (E)-β-santalol (1 and 2) and β-santalene (3a) which were obtained by total synthesis and, in addition, by isolation from East Indian sandalwood oil. - Key Words: Sandalwood oil / Fragrances / Stereoselective synthesis / β-Santalene, pure, isolation / Enantiomers, fragrance properties
