99212-15-4

Upstream product

• 99128-19-5 5,8-methano-3,4,4a,5,6,7,8,8a-octahydro-1H-2-benzopyran-1-one 
• 99128-20-8 (1S,2S,3R,4R)-3-(2-Phenylselanyl-ethyl)-bicyclo[2.2.1]heptane-2-carboxylic acid 
• 99128-18-4 (1SR,2RS,7SR,8RS)-4-oxatricyclo[6.2.1.0^2,7]undec-8-en-3-one 
• 542-92-7 cyclopenta-1,3-diene 
• 3393-45-1 5,6-dihydro-pyran-2-one 
• 186581-53-3 diazomethane 

Relevant academic research and scientific papers

Reductive, Radical-Induced Cyclizations of 5-Hexenals as a Biomimetic Model of the Chemistry of Secologanin Formation

A model reaction for studying the mechanism of the biological conversion of the iridoid loganin (1) to the secoiridoid secologanin (2) is the reductive, radical-induced cyclization of secologanin tetraacetate (4) to loganin tetraacetate.Treatment of 4 with Mg and Me3SiCl in THF at room temperature gives a mixture of the four possible C-6 and C-7 epimers of loganin tetraacetate in which the natural stereochemistry predominates.This result suggests that the biochemical event, which involves cleavage of the C-6 and C-7 bond of 1 in forming 2, may be a homolytic process that is initiated by formation of a carbon radical at C-8.The scope of the cyclization reaction, which formally occurred in a 5-hexanal moiety in 4, is defined by studies of the cyclization of six other δ,ε-unsaturated aldehydes.The results illustrate a new way for ring annulation through the reductive, radical-induced cyclization of δ,ε-unsaturated aldehydes.