154094-10-7Relevant academic research and scientific papers
Synthesis and Chemistry of Thia-analogs of the Anti-mitotic Podophyllium Lignans
McCombie, Stuart W.,Tagat, Jayaram R.,Metz, William A.,Nazareno, Dennis,Puar, Mohindar S.
, p. 8073 - 8086 (1993)
The Michael-aldol product (8) from PhSH-PhCHO-2(5H)-furanone is converted by acids to the tricyclic compound (9), without the intermediacy of the olefin (10).The podophyllotoxin analog (22) was similarly obtained.The all-trans compounds were isomerised by DBU to the cis lactones.Hydroxylated analogs (26) and (33) were produced by reacting 2-(5H)-furanone with appropriate 2-mercaptobenzophenones.Thermal rearrangement of the sulfoxide (35) initially gave the spirocyclic isomer (37), then formed dimeric products on prolonged heating.
