Tetrahedron p. 8073 - 8086 (1993)
Update date:2022-07-30
Topics:
McCombie, Stuart W.
Tagat, Jayaram R.
Metz, William A.
Nazareno, Dennis
Puar, Mohindar S.
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.
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