558472-46-1

Upstream product

• 501-53-1 benzyl chloroformate 
• 634902-49-1 toluenesulfonic acid (R)-1-methyl-but-3-enyl ester 
• 634902-50-4 (S)-4-azido-pent-1-ene 
• 64584-92-5 (R)-pent-4-en-2-ol 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 558472-49-4 (S)-3-[(benzyloxycarbonyl)amino]butyl aldehyde 

Downstream Products

• 558472-52-9 2-{(4S)-4-[(benzyloxycarbonyl)amino]pentyl}-5-butylfuran 
• 958887-71-3 (2S,6S)-2-methyl-6-undecyl-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 958887-75-7 (1S)-[5-(tert-butyldimethylsilanyloxy)-1-methyl-8-oxo-tetradec-3-enyl]carbamic acid benzyl ester 
• 958887-66-6 (1S)-(5-hydroxy-1-methylhexadec-3-enyl)carbamic acid benzyl ester 
• 558472-51-8 (2S)-2-(benzyloxycarbonyl)amino-6-methylene-9-oxotridecane 

Relevant academic research and scientific papers

Concise Enantioselective Synthesis of 3,5-Dialkyl-Substituted Indolizidine Alkaloids via Sequential Cross-Metathesis - Double-Reductive Cyclization

An efficient stereoselective synthesis of two 3,5-dialkyl-substituted indolizidine alkaloids is reported. The convergent syntheses are based on a novel sequence of a cross-metathesis (CM) reaction of an α,β -unsaturated ketone and a chiral homoallylic amine followed by a domino reaction involving hydrogenation, N-deprotection, and two diastereoselective reductive aminations. Our concept presents one of a few examples of a highly selective CM reaction in the synthesis of a natural product.

One-pot hydrogenation conditions for a sequential process to (+)-monomorine

(+)-Monomorine has been synthesized under mild hydrogenation conditions initiating deprotection followed by intramolecular, sequential reductive amination reactions. The precursors could be prepared concisely using B-alkyl Suzuki cross coupling of a chiral homoallylamine and a vinyl iodide or an iodofuran derivative.