936210-36-5

Upstream product

• 96405-61-7 goniodiol diacetate 
• 936210-34-3 (6S)-6-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-5,6-dihydro-2H-pyran-2-one 
• 936210-32-1 (1S)-1-[(4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-enyl acrylate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 1152590-02-7 C₁₆H₂₀O₄ 
• 665003-66-7 (1S)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 
• 122046-62-2 (S)-goniothalamin 
• 110044-45-6 (S)-6-((2R,3R)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one 
• 14371-10-9 (E)-3-phenylpropenal 
• 172925-28-9 trans-(S)-1-phenyl-1,5-hexadien-3-ol 

Downstream Products

• 96405-63-9 goniotriol triacetate 
• 96405-61-7 goniodiol diacetate 
• 96422-53-6 goniodiol monoacetate 

Relevant academic research and scientific papers

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.

Syntheses of all stereoisomers of goniodiol from yeast-reduction products and their antimicrobiological activity

All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.

Total synthesis and cytotoxicity of (+)- and (-)-goniodiol and 6-epi-goniodiol. Construction of α,β-unsaturated lactones by ring-closing metathesis

(+)-Goniodiol, a potent and selective cytotoxin, and (-)-6-epi-goniodiol, as well as their enantiomers, have been synthesized starting from cinnamyl alcohol. The key steps of the synthesis were Sharpless asymmetric epoxidation and cyclization of an acrylate derivative using ring-closing metathesis reaction. The cytotoxicity of both enantiomers of goniodiol and 6-epi-goniodiol against HL-60 cells was examined.

Structure and Stereochemistry of Four New 5,6-Dihydro-2-pyrones from Goniothalamus sesquipedalis and Goniothalamus grifithii

The leaves and twigs of Goniothalamus sesquipedalis Wall (Annonaceae) afford four new 6-(7,8-dihydrostyryl)-5,6-dihydro-2-pyrones, having in each case hydroxy and/or acetoxy functions at C-7 and C-8.The detailed high resolution PMR and other spectral analyses along with their chemical interconversions reveal their structures as 6-(7,8-dihydro-7,8-diacetoxystyryl)-5,6-dihydro-2-pyrone (II), 6-(7,8-dihydro-7-acetoxy-8-hydroxystyryl)-5,6-dihydro-2-pyrone (III), 6-(7,8-dihydro-7,8-dihydroxystyryl)-5,6-dihydro-2-pyrone (IV) and 6-(7,8-dihydro-7,8-dihydroxystyryl)-5,6-dihydro-5-hydroxy-2-pyrone (V).Compounds II, III and IV have also been isolated from the bark of Goniothalamus grifithii Hook.F and T.Thoms.The 7,8-erythro configuration is revealed for the above dihydropyrones from the coupling constants of the vicinal protons.Biogenetic considerations lead us to propose 6,7-threo and 7,8-erythro-configurations leading to 6(S), 7(S) and 8(S) configuration in these dihydropyrones.The stereochemistry of C-5 in V remains unsettled.