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First Total Synthesis of Enantiomerically Pure(−)‐Silphiperfol‐6‐en‐5‐on
Author(s) -
Demuth Martin,
Hinsken Werner
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710309
Subject(s) - chemistry , enantiomer , staring , enone , stereochemistry , communication , sociology
The angular triquinane (−)‐silphiperfol‐6‐en‐5‐on ((−)‐ 14 ) has been synthesized for the first time time in enantiomerically pure form. A highly efficient triplet‐sensitized photoreaction, the oxadi‐π‐methane rearrangement of the complex β,γ‐enone(+)‐ 6 to (−)‐ 7 , constitutes the key step. The know staring material, (1 R , 7a R )‐3,6,7,7a‐tetrahydro‐1‐hydroxy‐7a‐methyl‐1 H ‐inden‐5(2 H )‐one ((−)‐ 2 ), is readily accessible in > 97% enantiomeric purity. This new approach should enable access also to other angularly fused triquinanes of the silphinene type and related structures.