SYNTHESIS AND CHEMISTRY OF THIA-ANALOGS OF THE ANTI-MITOTIC PODOPHYLLIUM LIGNANS

Authors
MCCOMBIE SW TAGAT JR METZ WA NAZARENO D PUAR MS
Citation
Sw. Mccombie et al., SYNTHESIS AND CHEMISTRY OF THIA-ANALOGS OF THE ANTI-MITOTIC PODOPHYLLIUM LIGNANS, Tetrahedron, 49(36), 1993, pp. 8073-8086
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
36
Year of publication
1993
Pages
8073 - 8086
Database
ISI
SICI code
0040-4020(1993)49:36<8073:SACOTO>2.0.ZU;2-W
Abstract
The Michael-aldol product (8) from PhSH-PhCHO-2(5H)-furanone is conver ted by acids to the tricyclic compound (9), without the intermediacy o f the olefin (10). The podophyllotoxin analog (22) was similarly obtai ned. The all-trans compounds were isomerised by DBU to the cis lactone s. Hydroxylated analogs (26) and (33) were produced by reacting 2-(5H) -furanone with appropriate 2-mercaptobenzophenones. Thermal rearrangem ent of the sulfoxide (35) initially gave the spirocyclic isomer (37), then formed dimeric products on prolonged heating.