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Synthesis and Absolute Configuration of Naturally Occurring Dactyloxene‐B and ‐C
Author(s) -
Maurer Bruno,
Hauser Arnold,
Ohloff Günther
Publication year - 1980
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.19800630844
Subject(s) - chemistry , absolute configuration , cyclohexene , stereochemistry , absolute (philosophy) , organic chemistry , catalysis , philosophy , epistemology
Natural (+)‐dactyloxene‐B (12) and ‐C (13) have been synthesized starting from (+)‐ trans ‐2, 5, 6‐trimethyl‐l‐cyclohexene‐l‐carbaldehyde (1) which is shown to have the (5 S , 6 R )‐configuration by chemical correlation with (+)‐(2 R , 3 S , 6 S )‐2, 3, 6‐trimethylcyclohexanone. The absolute configurations are therefore (2 R , 5 R , 9 S , 10 R ) for (+)‐dactyloxene‐B and (2 R , 5 S , 9 S , 10 R ) for (+)‐dactyloxene‐C.