462629-89-6

Upstream product

• 917-54-4 methyllithium 
• 90865-69-3 (3S)-4-Benzyloxy-3-methyl-butyraldehyde 
• 462629-88-5 (3aS,5R, 6R,6aS)-6-Methyl-5-vinyl-4,5,6,6a-tetrahydro-3a-H-pentalen-1-one 
• 15681-48-8 dimethyllithium cuprate 
• 391208-05-2 (S)-1-((2-methylpent-4-enyloxy)methyl)benzene 
• 462629-92-1 (1S,2S,3R,4R)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid methoxymethylamide 
• 184591-90-0 (1S,2S,3R,4R)-1-(3-methylbicyclo[2.2.1]hept-5-ene-2-yl)propenone 
• 127179-45-7 (2-endo,3-exo)-3-methyl-bicyclo[2,2,1]hept-5-ene-2-carboxylic acid 
• 100-39-0 benzyl bromide 
• 5673-98-3 (S)-(-)-2-methyl-4-penten-1-ol 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of Dendrobatid Alkaloids: Preparation of Indolizidine 251F and Its 3-Desmethyl Analogue Using an Intramolecular Schmidt Reaction Strategy

Total syntheses of alkaloid 251F (1), a natural product detected from the skin extracts of the dendrobatid frog species Minyobates bombetes, and its racemic 3-desmethyl derivative (2) are reported. A Diels-Alder reaction initiated both syntheses and established four consecutive stereogenic centers. Important to the synthesis of 2 was a first-generation ozonolysis/olefination/aldol strategy to convert a [2.2.1] bicyclic acid to the [3.3.0]bicyclooctane diquinane 4b. Further elaboration to an appropriate keto azide allowed for a key intramolecular Schmidt reaction to deliver the tricyclic core of the target molecule. In a second-generation approach, a tandem ring-opening/ring-closing metathesis reaction effected an overall [2.2.1] → [3.3.0] skeletal rearrangement to deliver diquinane 4a. In similar fashion, 4a was manipulated to an appropriate keto azide, and an intramolecular Schmidt reaction generated the core cyclic architecture of 251F.