Function-oriented synthesis: studies aimed at the synthesis and mode of action of 1alpha-alkyldaphnane analogues.
[reaction: see text] An efficient synthetic route to the ABC tricyclic core of 1alpha-alkyldaphnanes has been developed. The conformational bias imparted by the C6-C9 oxo-bridge of BC-ring system 12 was used to elaborate the ABC-ring system precursor including the introduction of the beta-C5 hydroxyl group. A completely diastereoselective palladium-catalyzed enyne cyclization was then employed to establish the A-ring with a C1 appendage.
Wender
Paul A
PA
Department of Chemistry and Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu
D'Angelo
Noel
N
Elitzin
Vassil I
VI
Ernst
Martin
M
Jackson-Ugueto
Eileen E
EE
Kowalski
John A
JA
McKendry
Sharon
S
Rehfeuter
Markus
M
Sun
Robert
R
Voigtlaender
David
D
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D004224:Diterpenes; C011309:mezerein