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Efficient and diastereoselective synthesis of (+)‐ and (−)‐grandisol and 2‐[(1 R ,2 S )‐2‐isopropenylcyclobutyl]ethanol (demethylgrandisol) in high purity
Author(s) -
Hoffmann Norbert,
Scharf HansDieter
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101219
Subject(s) - chemistry , diastereomer , cyclobutanes , yield (engineering) , ethanol , acetone , ethylene , stereochemistry , organic chemistry , cyclobutane , ring (chemistry) , catalysis , materials science , metallurgy
Acetone‐sensitized [2 + 2] photocycloaddition of ethylene to chiral butenolides 3 and 15 yields diastereomeric cyclobutanes, which are transformed to (+)‐( 1 ) and (−)‐grandisol ( ent ‐ 1 ) (overall yield 34–36%) and to 2‐[(1 R ,2 S )‐2‐isopropenylcyclobutyl]ethanol (demethylgrandisol) ( 2 ) (overall yield 25%) in five steps.