153870-91-8

Upstream product

• 1504-56-9 (E)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 71277-13-9 3,4,5-trimethoxycinnamaldehyde 
• 20329-96-8 methyl 3,4,5-trimethoxycinnamate 
• 125730-98-5 (RS)-6-<1'-benzoyloxy-3'-(3'',4'',5''-trimethoxyphenyl)propyl>-2-methoxycyclohepta-2,4,6-trienone 
• 153870-90-7 (RS)-6-<1'-hydroxy-3'-(3'',4'',5''-trimethoxyphenyl)propyl>-2-methoxycyclohepta-2,4,6-trienone 

Relevant academic research and scientific papers

Fully Regiocontrolled Synthesis of (+/-)-12a,12b-Secocolchicine and Studies Concerning its Cyclisation to the Alkaloid Colchicine

A fully regiocontrolled synthesis of the title compound 6, an AC-ring analogue of the alkaloid colchicine 1, is reported.The key step associated with the sequence used was condensation of lithium halogenocarbenoid 10 - a synthetic equivalent for the inaccessible 7-methoxytropon-3-yl anion 12-with 3,4,5-trimethoxycinnamaldehyde 17 to produce the 1,2-addition product 18 as a mixture of diastereoisomers.Elaboration of compound 18 provided benzoate 23 which, on treatment with base, underwent ring-expansion to give troponoid 24 in excellent yield.Replacement of the C-7 benzoate group in compound 24 by an acetamido moiety was readily achieved and produced compound 6 in good overall yield.Unsuccessful attempts to convert compound 6 and the deacetamido analogue 38 into colchinine and deacetamidocolchicine 3, respectively, are described.