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- Title
Synthesis and Circular Dichroism of Optically Pure (±)-(1 S,2 S,5 S)-5-Methoxy-3,4,6,7-tetramethylidenebicyclo[3.2.1]oct-2-yl Derivatives. Baker's Yeast Reduction of 4-Methoxy-5,6,7,8-tetramethylidenebicyclo[2.2.2]octan-2-one.
- Authors
Burnier, Gérald; Vogel, Pierre
- Abstract
Baker's yeast reduction of 4-methoxy-5,6,7,8-tetramethylidenebicyclo[2.2.2]octan-2-one ( 11) under fermenting conditions afforded (−)-(1 S,2 S,4 R)-4-methoxy-5,6,7,8-tetramethylidenebicyclo[2.2.2]octan-2-ol ((−)- 13) in 60% yield with an e.e. > 99.5%. Its methanesulfonate (−)- 14 was hydrolyzed and rearranged with high stereo-selectivity into (+)-(1 S,2 S,5 S)-5-methoxy-3,4,6,7-tetramethylidenebicyclo[3.2.1]octan-2-ol ((+)- 15). The absolute configuration of (−)- 13 was deduced from the CD spectrum of its 4-(dimethylamino)benzoate ((+)- 22) applying the chiral exciton-coupling method. The CD spectrum of (+)- 15 and of its ( tert-butyl)dimethylsilyl ether ((+)- 23) showed exciton-split type of Cotton effects attributed to through-space interactions between the s- gauche-buta-diene and s- cis-butadiene chromophores of these systems.
- Publication
Helvetica Chimica Acta, 1990, Vol 73, Issue 4, p985
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19900730425