665003-66-7Relevant articles and documents
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.
Cytotoxic activity of (S)-goniothalamin and analogues against human cancer cells
De Fatima, Angelo,Kohn, Luciana K.,De Carvalho, Joao Ernesto,Pilli, Ronaldo A.
, p. 622 - 631 (2007/10/03)
(R)- and (S)-Goniothalamin (1) and analogues 2-9 were efficiently prepared in high overall yield and enantiomeric purity, and their cytotoxic activities were evaluated against eight human cancer cell lines. A structure-activity relationship study (SAR) al
Asymmetric allylboration for the synthesis of β-hydroxy-δ-lactone unit of statin drug analogs
Reddy, M. Venkat Ram,Brown, Herbert C.,Ramachandran, P. Veeraraghavan
, p. 239 - 243 (2007/10/03)
Acrylic esters of homoallylic alcohols prepared in 92-96% ee via the asymmetric allylboration of appropriate aldehydes with B-allyldiisopinocampheylborane, upon ring-closing metathesis in the presence of 10mol% of Grabbs' catalyst provided the correspondi
