1428535-20-9

Upstream product

• 1428535-16-3 (3S,6aR,8aR,9R,12aR,12bR)-methyl 3,12a-dimethyl-5-oxotetradecahydro-1H-3,6a-methanonaphtho[2,1-d]azocine-9-carboxylate 
• 100-39-0 benzyl bromide 
• 672948-33-3 (4R,4aS,6aR,9S,11aR,11bS,E)-methyl 8-(benzylimino)-4,9,11b-trimethyltetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate 
• 672948-32-2 (4R,4aS,6aR,9S,11aR,11bS,E)-methyl 8-(hydroxyimino)-4,9,11b-trimethyltetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate 
• 1428535-14-1 (1R,4aR,4bR,8aR,10aR)-methyl 8a-(cyanomethyl)-4a,7-dimethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylate 
• 30217-41-5 isosteviol methyl ester 
• 27975-19-5 isosteviol 

Relevant academic research and scientific papers

Diversity-Oriented Library Synthesis from Steviol and Isosteviol-Derived Scaffolds

The readily available natural product stevioside provides a unique diterpene core structure that can be explored for small molecule library development by diversity-oriented synthesis and functional group transformations. Validation arrays were prepared from steviol, isosteviol, and related analogues, derived from stevioside, to produce over 90 compounds. These compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for screening in the Molecular Libraries Screening Center Network. Micromolar hits were identified in multiple high-throughput assays for several library members. A cheminformatics analysis of the compounds was performed that verified the expected diversity and complexity of this set of compounds. The screening results indicate that scaffolds-derived natural products can provide screening hits against multiple target proteins.

Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol

We have applied a diversity-oriented approach for the synthesis of skeletally diverse and stereochemically complex templates for small-molecule library production by performing Beckmann rearrangement and Beckmann fragmentation reactions on the bicyclo[3.2.1]octane rings of steviol and isosteviol, aglycones derived from the diterpene natural product stevioside. The optimization of these two reaction pathways is presented along with the successful application of a photo-Beckmann rearrangement. This work also led to the discovery of cyano-Prins-type and Thorpe-Ziegler-type cyclization reactions.