Canadian Journal of Chemistry p. 1076 - 1083 (1997)
Update date:2022-07-31
Topics:
Charlton, James L.
Chee, Gaik-Lean
A simple procedure for the asymmetric synthesis of lignans via chiral β-benzyl-γ-butyrolactones has been developed. The key benzylbutyrolactone intermediates were efficiently synthesized using a six-step procedure, starting from 3,4-(methylenedioxy)cinnamic acid. The key step in this sequence was a highly diastereoselective alkylation of an N-acyloxazolidinone enolate. The resulting β-benzyl-γ-butyrolactones were subsequently transformed into the benzylidene lignans gossypifan and savinin (hibalactone) via aldol condensation-dehydration reactions, and into the dibenzylbutyrolactone lignan 4′-demethylyalein, through alkylation. Oxidation of 4′-demethylyatein with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) afforded cis- and trans-benzylidenebenzylbutyrolactones, whereas oxidation with DDQ/TFA gave 4′-demethyl-deoxyisopodophyllotoxin.
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