(R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines.
The total syntheses of (R)-goniothalamin (1), a styryl lactone isolated from several Goniothalamus species, via catalytic asymmetric allylation of alpha-benzyloxyacetaldehyde (2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of trans-cinnamaldehyde (12), followed by ring-closing metathesis are reported. The antiproliferative activities of (R)-1 and its Z-isomer 10 as well as of the synthetic dihydropyranone intermediates 7 and 8 against eight different cancer cell lines are also described.
de Fátima
Angelo
A
Instituto de Química, Unicamp, CP 6154, 13084-971, Campinas, São Paulo, Brazil.
Kohn
Luciana Konecny
LK
Antônio
Márcia Aparecida
MA
de Carvalho
João Ernesto
JE
Pilli
Ronaldo Aloise
RA
D029061:Annonaceae / Q000737:chemistry; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008968:Molecular Conformation; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
D011753:Pyrones; C103280:goniothalamin