1152589-20-2

Upstream product

• 172925-28-9 trans-(S)-1-phenyl-1,5-hexadien-3-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 916151-83-2 (S)-6-((2S,3S)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one 
• 122046-62-2 (S)-goniothalamin 
• 665003-66-7 (1S)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 

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.