916151-83-2Relevant academic research and scientific papers
First total synthesis of the highly potent antitumor lactones 8-chlorogoniodiol and parvistone A: Exploiting a bioinspired late-stage epoxide ring-opening
Ramesh, Perla,Narasimha Reddy, Yarram,Narendar Reddy, Thatikonda,Srinivasu, Navuluri
supporting information, p. 246 - 249 (2017/02/15)
The first protecting group-free total syntheses of the highly potent antitumor chlorinated styryllactone secondary metabolites 8-chlorogoniodiol, parvistone A, and one analogue 8-epi-parvistone A, have been accomplished from commercially available trans-cinnamaldehyde in five steps with high overall yields. The chlorine-bearing stereogenic center of these silent secondary metabolites was introduced via a bioinspired late-stage regioselective epoxide ring-opening strategy. Maruoka asymmetric allylation, acrylation, ring-closing metathesis and asymmetric epoxidation, greatly facilitate the synthesis of the key intermediates goniothalamin oxide and (6S,7S,8S)-isogoniothalamin oxide.
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.
Asymmetric total synthesis and antiproliferative activity of goniothalamin oxide isomers
Marquissolo, Cilene,Fatima, Angelo de,Kohn, Luciana K.,Ruiz, Ana Lucia T.G.,Carvalho, Joao Ernesto de,Pilli, Ronaldo A.
experimental part, p. 52 - 56 (2009/07/18)
Goniothalamin oxide (1) is a styryl lactone which was isolated from bark and leaves of several Goniothalamus species. This natural product has some interesting biological properties such as larvicidal and tripanocidal activities. However, no studies on th
GONIOTHALAMIN OXIDE: AN EMBRYOTOXIC COMPOUND FROM GONIOTHALAMUS MACROPHYLLUS (ANNONACEAE)
Sam, T. W.,Sew-Yeu, Chew,Matsjeh, Sabirin,Gan, E. K.,Razak, Dzulkifli,Mohamed, Abdul L.
, p. 2541 - 2544 (2007/10/02)
Goniothalamin (1) and its oxide (2) have been isolated as the active embryotoxic and teratogenic components of the title plant.The structure of goniothalamin oxide (2) was established from its spectral data and its synthesis together with an isomer (3) by
