Tetrahedron

Synthesis and chemistry of thia-analogs of the anti-mitotic podophyllium lignans

SW McCombie, JR Tagat, WA Metz, D Nazareno…

Index: McCombie, Stuart W.; Tagat, Jayaram R.; Metz, William A.; Nazareno, Dennis; Puar, Mohindar S. Tetrahedron, 1993 , vol. 49, # 36 p. 8073 - 8086

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Citation Number: 18

Abstract

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 ...