51686-50-1Relevant articles and documents
Novel conformationally restricted tetracyclic analogs of δ8- tetrahydrocannabinol
Khanolkar, Atmaram D.,Lu, Dai,Fan, Pusheng,Tian, Xiaoyu,Makriyannis, Alexandros
, p. 2119 - 2124 (1999)
Novel analogs of (-)-Δ8-tetrahydrocannabinol (Δ8-THC) in which the conformation of the side chain was restricted by incorporating the first one or two carbons into a six membered ring fused with the aromatic phenolic A ring were synt
Methods for the Construction of Linear 1,7-Diarylheptanoids; Synthesis of Di-O-methylcentrolobol and Precursors (Synthetic and Biosynthetic) to the meta,meta-Bridged Biphenyls Myricanol and Myricanone
Henley-Smith, Peter,Whiting, Donald A.,Wood, Andrew F.
, p. 614 - 622 (2007/10/02)
1,7-diarylheptanoids are a varied natural product class in which 'linear' types appear to be biosynthetic precursors to macro(carbo)cyclic (3), macro(oxa)cyclic (4), and condensed polycyclic (5) examples.Various methods (suitable for radiolabelling) are described for constructing 'linear' diarylheptanoids, including Grignard couplings (employing activated magnesium) with arylpropanals and oxazonium salts (11a), (11h), (15a), and (15b)> and dithian alkylation (15c)>.Alkyl-lithium treatment of the benzyloxydithian (19b) gave 1,2,3-triphenylcyclopropane.Syntheses via trialkylcyanoborates were frustrated by disproportionation of the intermediate trialkylboranes.The diarylheptanoids synthesised (11a-h) and (15a-e) include synthetic and biosynthetic precursors to meta,meta-bridged biphenyls and related macrocyclic ethers.