74164-84-4

Usage

InChI:InChI=1/C8H13NO/c1-6-2-4-9-5-3-7(10)8(6)9/h7-8,10H,1-5H2/t7-,8-/m1/s1

Upstream product

• 1053612-38-6 (3R,4R)-4-Amino-5-methylene-heptane-1,3,7-triol 
• 59084-35-4 1-chloromethyl-1,2-didehydro-7β-hydroxy-8α-pyrrolizidine hydrochloride 
• 480-54-6 retrorsine 
• 480-85-3 retronecine 
• 187103-26-0 Acetic acid 4-acetoxy-2-{(4S,5R)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-trichloromethyl-4,5-dihydro-oxazol-4-yl}-2-iodo-butyl ester 
• 187103-23-7 Acetic acid (Z)-(R)-2-(2-acetoxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-hex-2-enyl ester 
• 187103-21-5 Acetic acid (E)-(R)-2-(2-acetoxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-hex-2-enyl ester 
• 1025964-39-9 Acetic acid (Z)-(R)-2-(2-acetoxy-ethyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-(2,2,2-trichloro-acetimidoyloxy)-hex-2-enyl ester 

Relevant academic research and scientific papers

Confirmation of the stereochemistry of 7β-angelyl-1-methylene-8α-pyrrolizidine

The (7R,8R) stereochemistry of naturally occurring 7β-angelyl-1-methylene-8α-pyrrolizidine 1 was confirmed by subjecting a mixture of a synthetic standard and the natural product to various chiral differentiating techniques. The synthetic 7β-angelyl-1-methylene-8α-pyrrolizidine 1 was prepared from enantiomerically pure retronecine 3.

An enantiocontrolled synthesis of pyrrolizidines, (-)-platynecine and (-)-hadinecine

Trisubstituted allylic alcohols 13 and 14 have been converted into a single isomeric trans-oxazoline 16 via an intramolecular iodoamidation of the corresponding trichloroacetimidates, which have been elaborated into (-)-platynecine 1 and(-)-hadinecine 2 via a common intermediate pyrrolizidine.