4'-Oxa-a-santalene and 4'-oxa-a-santalol: an olfactory comparison with the analogous natural sesquiterpenes

Allyl type organometallic intermediates allow the prepn. of the 4'-oxa analogs I (R = H, OH, X = O) of a-santalene (I; R = H, X = CH2) and a-santalol (I; R = OH, X = CH2) in a very convenient, regio- and stereocontrolled manner from bromotricyclene (II). The introduction of the heteroatom into the side chain of the natural fragrances changes the smelling properties profoundly. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 34, 39, 6265-8
Year:
1993
Keywords:
Note:
CAN 120:192019
30-15
Terpenes and Terpenoids
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
written in English.
513-42-8 (2-Methyl-2-propen-1-ol) Role: RCT (Reactant), RACT (Reactant or reagent) (O-metalation and reaction of, with bromotricyclene); 153140-62-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and isomerization, or stereo- and regiocontrolled hydroxylation of); 115-71-9DP (a-Santalol); 512-61-8DP (a-Santalene); 153140-60-4P; 153140-61-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and olfactive properties of); 153140-63-7P; 153140-64-8P; 153220-91-8P; 153220-92-9P; 153220-93-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 52645-83-7 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with potassium methylpropenolate)
Laboratories:




 Record created 2006-03-03, last modified 2018-12-03


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