The asymmetric synthesis of an isomer of podophyllotoxin
1994; Elsevier BV; Volume: 50; Issue: 36 Linguagem: Inglês
10.1016/s0040-4020(01)89274-7
ISSN1464-5416
AutoresAndrew Pelter, Robert S. Ward, Neil P. Storer,
Tópico(s)Traditional and Medicinal Uses of Annonaceae
ResumoTandem conjugate addition by an O-silylcyanohydrin derived carbanion to 5-(1-menthyloxy)-2(5H)-furanone, followed by reaction with an aromatic aldehyde gives two diastereoisomeric adducts. These afford a single product on treatment with tetrabutylammonium fluoride. Reduction with concomitant removal of the menthyloxy group, followed by acid catalysed cyclisation gave a homochiral tetrahydronaphthalene retro-lactone which is an interesting structural isomer of podophyllotoxin.
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