122046-63-3

Upstream product

• 22639-28-7 (R)-goniothalamin 
• 1174166-03-0 (1R)-1-[(2S,3S)-3-phenyloxiran-2-yl]but-3-en-1-yl acrylate 
• 14371-10-9 (E)-3-phenylpropenal 
• 639798-55-3 (1R)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 
• 13891-95-7 (1E,3R)-1-phenyl-1,5-hexadien-3-ol 
• 104-55-2 3-phenyl-propenal 
• 1743-31-3 (E)-1-phenylhex-1-en-5-yn-3-ol 
• 17303-67-2 (2'E)-6-(2'phenylvinyl)-5,6-dihydro-2H-pyran-2-one 
• 129694-45-7 (2S)-6-Hydroxy-2-<(E)-styryl>-6H-pyran-3(2H)-one 
• 128229-81-2 (E)-1-(furan-2-yl)-3-phenylprop-2-en-1-ol 
• 231963-90-9 (R)-6-((tert-butyl(dimethyl)silyloxy)methyl)-5,6-dihydropyran-2-one 
• 445289-97-4 (R)-1-((tert-butyldiphenylsilyl)oxy)pent-4-en-2-yl acrylate 
• 206651-83-4 (R)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-5,6-dihydro-2H-pyran-2-one 
• 89408-85-5 (6R)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one 

Downstream Products

• 146236-73-9 (+)-goniodiol 

Relevant 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

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.

Protecting-Group-Free Total Synthesis of 8-Methoxygoniodiol

A concise stereoselective total synthesis of the naturally occurring styryl lactone 8-methoxygoniodiol in five simple steps from readily available inexpensive trans-cinnamaldehyde is described. The efficient synthesis features a successful protecting-group-free strategy, with desirable step- and atom-economy. The synthetic strategy relies on a Maruoka asymmetric allylation, an epoxidation, a ring-closing metathesis, and a stereoselective epoxide ring opening as key steps.

Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e

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

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

Asymmetric total synthesis and antiproliferative activity of goniothalamin oxide isomers

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

A concise enantioselective strategy to (+)-(R)-goniothalamin and (+)-(R)-goniothalamin oxide by employing hydrolytic kinetic resolution and ring-closing metathesis as key steps

An efficient and general strategy to (R)-goniothalamin and (R)-goniothalamin oxide is described by using Jacobsen's hydrolytic kinetic resolution of racemic epoxide and ring-closing metathesis (RCM) as key steps, which provided a rapid access to these natural products that display a fascinating array of biological activity. (R)-Goniothalamin oxide was prepared in high yield and diastereomeric excess under various epoxidation conditions. Georg Thieme Verlag Stuttgart.

Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis

A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity.

Facile enantioselective synthesis of 6R-(+)-goniothalamin and (6R, 7R, 8R)-(+)-goniothalamin oxide

Facile enantioselective total syntheses of 6R-(+)-goniothalamin 1 and (6R, 7R, 8R)-(+)-goniothalamin oxide 2 were achieved through the Sharpless kinetic resolution of racemic secondary 2- furylmethanol 3 in a short synthetic route.

Styrylpyrone Derivatives from Goniothalamus dolichocarpus

Styrylpyrone derivatives (+)-goniothalamin (1), (+)-goniothalamin epoxide (2) and (-)-iso-5-deoxygoniopypyrone (4b), and the acetogenin (+)-annonacin (7) were bioactive compounds isolated from the stem bark of Goniothalamus dolichocarpus.The stereochemica

Stereochemistry of baker's yeast mediated reduction of α,β-unsaturated δ-lactones in the goniothalamin series

Baker's yeast reduction of racemic α,β-unsaturated δ-lactones 5, 6 and 7 proceeds with kinetic preference for the (S) enantiomers. The procedure allows the obtainment of enantiomerically pure (+)-(R)-goniothalamin 5.