872832-12-7

Upstream product

• 67496-29-1 1-bromo-6-aminomethyl-3,4-(methylenedioxy)-benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 872831-66-8 (benzyl)(6-bromobenzo[1,3]dioxol-5-ylmethyl)(4-methoxybenzyl)amine 
• 872832-11-6 (6-bromobenzo[1,3]dioxol-5-ylmethyl)(4-methoxybenzyl)amine 
• 872831-67-9 6-{[(benzyl)(4-methoxybenzyl)amino]methyl}-benzo[1,3]dioxol-5-carboxaldehyde 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 

Downstream Products

• 872832-13-8 (6-{[(benzyl)(4-methoxybenzyl)amino]methyl}-benzo[1,3]dioxol-5-yl)acetaldehyde 

Relevant academic research and scientific papers

Asymmetric total synthesis of the 1-epi-aglycon of the cripowellins A and B

The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epi-aglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee ≥ 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.