86046-97-1Relevant academic research and scientific papers
Side chain methyl analogues of Δ8-THC
Huffman, John W.,Lainton, Julia A.H.,Banner, W. Kenneth,Duncan Jr., Sammy G.,Jordan, Robert D.,Yu, Shu,Dai, Dong,Martin, Billy R.,Wiley, Jenny L.,Compton, David R.
, p. 1557 - 1576 (2007/10/03)
The synthesis of both side chain epimers of 1'- (4), 2'- (5), 3'-methyl- (6) and 4'-methyl-Δ8-tetrahydrocannobinol (7) has been carried out. The synthetic approach entailed the acid catalyzed condensation of the appropriate substituted resorcinol with menthadienol to provide the Δ8-THC analogue. Both isomers of 1'- (4) and 2'-Δ8-THC (5) were more potent than Δ8-THC, both in vitro and in vivo. The 3'-methyl isomers (6) were approximately equal in potency to Δ8-THC, and 4'-methyl-Δ8-THC was less potent. There was relatively little difference in potency between the epimers of 4, 5, and 6.
Total synthesis of (-)-maysine
Meyers,Babiak,Campbell,et al.
, p. 5015 - 5024 (2007/10/02)
A convergent synthesis of the natural macrocycle (-)-maysine (3) has been accomplished involving only a single separation of epimers at C-10. The scheme involved the preparation of three major fragments: (a) the western zone, 4; (b) the southern zone, 6;
ENANTIOSELECTIVE SYNTHESIS OF C3-C10 FRAGMENT (NORTHEASTERN ZONE) OF MAYTANSINOIDS WITH 4-CHIRAL CENTERS (4S,5S,6R,7S)
Meyers, A. I.,Hudspeth, James P.
, p. 3925 - 3928 (2007/10/02)
The major precursor to the maytansinoids containing 4 non-racemic chiral centers has been prepared in gram quantities, suitable for further synthesis.The route to (+)-1 was accomplished in 13 steps including several highly stereocontrolled reactions which
