872831-89-5

Upstream product

• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 38336-04-8 O-benzylethanolamine 

Downstream Products

• 872831-98-6 tert-butyl N-(2-(benzyloxy)ethyl)-N-((6-bromo-1,3-benzodioxol-5-yl)methyl)carbamate 
• 872831-88-4 (4S,5R)-2,2-Dimethyl-5-(2-oxo-propyl)-[1,3]dioxolane-4-carboxylic acid (2-benzyloxy-ethyl)-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-amide 

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.