17690-54-9

Upstream product

• 480-85-3 retronecine 
• 82485-07-2 9-O-(tert-Butyldimethylsilyl)retronecine 
• 35660-94-7 (Z)-2-methyl-2-butenoyl chloride 
• 377076-03-4 2-methyl-but-2-enoic acid 7-(tert-butyl-dimethyl-silanyloxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester 
• 95462-11-6 (4S,5S)-4-Isopropyl-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 
• 100101-27-7 7-angelyl-9-l-viridiflorylheliotridine 

Relevant academic research and scientific papers

Ester alkaloids of Heliotropium bracteatum

Isolation and structure determination of the two new ester alkaloids of Heliotropium bracteatum, viz. helibracteatinine and helibracteatine, are described.Helibracteatinine was formulated as 1β-hydroxymethyl-7α-angelyloxy-8α-pyrrolizidine-1α-ol and helibracteatine as 1β-angelyloxy-8α-pyrrolizidine-1α,7α-diol.Structures were established by spectrometry of the alkaloids and by hydrolysis to their necine bases.

Reactive enols in synthesis 2. Synthesis of (+)-latifolic acid and (+)-latifoline

We describe a short, enantioselective synthesis of the naturally occurring pyrrolizidine alkaloid (+)-latifoline (1) employing a tandem [3,3] sigmatropic rearrangement/[1,2] allyl shift as a key step in constructing (+)-latifolic acid (4).

THE SYNTHESIS OF HELIOTRIDINE AND RELATED ALKALOIDS

An efficient synthesis of heliotridine from readily available retronecine was accomplished by nucleophilic displacement of the 7-mesylate, in the 7-mesyl-9-benzoate of retronecine with various cesium carboxylates in DMF, followed by hydrolysis.The synthet