Studies toward the total synthesis of Wiedemannic acid.
[reaction: see text] We report a novel and efficient diastereoselective synthesis of wiedemannic acid analogue 30 in 16 steps from 7 using a tandem oxy-Cope/Claisen/ene reaction as the key step. Comparison of NMR data between wiedemannic acid (1) and analogue 30 leads us to believe that the reported stereochemistry at the ring junction of 1 is incorrect.
Sauer
Effiette L O
EL
Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Canada K1N 6N5.
Barriault
Louis
L
D045784:Abietanes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry; D027544:Salvia / Q000737:chemistry
D045784:Abietanes; C503893:wiedemannic acid