639798-55-3Relevant articles and documents
(R)-Goniothalamin: Total syntheses and cytotoxic activity against cancer cell lines
De Fatima, Angelo,Kohn, Luciana Konecny,Antonio, Marcia Aparecida,De Carvalho, Joao Ernesto,Pilli, Ronaldo Aloise
, p. 2927 - 2933 (2005)
The total syntheses of (R)-goniothalamin (1), a styryl lactone isolated from several Goniothalamus species, via catalytic asymmetric allylation of α-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.
Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e
Ramesh, Perla,Rao, Tadikamalla P.
, p. 2060 - 2065 (2016/09/09)
A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation. The route is amenable to synthesis of various analogues for biological evaluation.
De novo asymmetric syntheses of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin using asymmetric allylations
Harsh, Philip,O'Doherty, George A.
experimental part, p. 5051 - 5055 (2009/12/01)
A highly enantio- and diastereoselective approach to either enantiomer of (+)-goniothalamin, (+)-goniothalamin oxide, and 7,8-bis-epi-goniothalamin oxide has been developed from achiral cinnamyl alcohol or cinnamaldehyde. The asymmetry of the synthesis wa
