A short and simple access to both enantiomers of epi-b-santalene and (Z)-epi-b-santalol

Epi-b-santalene (I; R = H), readily accessible in both enantiomeric forms, was regio- and stereoselectively converted into (R)-(-)- or (S)-(+)-(Z)-epi-b-santalol (I; R = OH) by consecutive metalation, borylation and oxidn. [on SciFinder (R)]


Published in:
Synlett, 3, 173-4
Year:
1994
Keywords:
Note:
CAN 121:109300
30-15
Terpenes and Terpenoids
Inst. Chim. Org. Univ.,Lausanne,Switz.
Journal
0936-5214
written in English.
129704-42-3; 156617-34-4 Role: RCT (Reactant), RACT (Reactant or reagent) (acid-catalyzed rearrangement of, in synthesis of epi-b-santalol); 464-48-2 ((-)-Camphor); 464-49-3 ((+)-Camphor) Role: PROC (Process) (conversion of, to epi-b-santalol); 78247-51-5P; 78247-53-7P Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, in synthesis of epi-b-santalol); 563-45-1 (3-Methyl-1-butene) Role: RCT (Reactant), RACT (Reactant or reagent) (metalation and reaction of, withbromocamphenes); 25532-78-9P ((+)-epi-b-Santalene); 156617-33-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and conversion of, to epi-b-santalol); 156539-28-5P; 156617-31-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and diastereomeric excess detn. of); 129704-45-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with prenylpotassium); 156617-32-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with prenylpotassium in synthesis of epi-b-santalol); 10293-09-1P; 64474-56-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of, in synthesis of epi-b-santalol); 42495-69-2P; 98718-54-8P Role: PREP (Preparation) (regio- and stereoselective total synthesis of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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