319915-03-2

Upstream product

• 89272-56-0 (4R)-4,8-dimethyl-7-nonen-2-one 
• 319915-06-5 Methanesulfonic acid (R)-4-methyl-5-(2-methyl-[1,3]dioxolan-2-yl)-pentyl ester 
• 136155-10-7 (R)-6,6-Ethylenedioxy-4-methyl-1-heptanol 
• 136155-14-1 (R)-6,6-Ethylenedioxy-1-iodo-4-methylheptane 
• 123487-14-9 (6R)-2,6-dimethyl-8,8-(ethylenedioxy)-2-nonene 
• 18951-85-4 (R)-citronellic acid 
• 162662-10-4 2-Methyl-2-((R)-2-methyl-pent-4-enyl)-[1,3]dioxolane 

Downstream Products

• 319915-13-4 Toluene-4-sulfonic acid (2R,4R,6R,8S)-4,8-dimethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl ester 

Relevant academic research and scientific papers

Synthesis and stereochemistry of insect derived spiroacetals with branched carbon skeletons

About thirty constitutionally different spiroacetals have been characterised from insects but only three have branched carbon skeletons. Two are based on the 1,7-dioxaspiro[5.5]undecane system and are certain stereoisomers of the 2,4,8-trimethyl derivative, from the aposematic shield bug, Cantao parentum (White), and a 2,2,8-trimethyl derivative from the rove beetle, Ontholestes murinus (L). The 1,6-dioxaspiro[4.5]decane system is represented by a stereoisomer of the 2,3,7-trimethyl derivative in the Cantao species. The elucidation of their structures and stereochemistry by spectroscopy, synthesis and enantioselective gas chromatography is described.

From (R)-(+)-pulegone to (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro[5.5]undecane - A unique spiroacetal from the insect kingdom

Enantioselective syntheses of the unique, insect-derived spiroacetal, (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro[5.5]undecane and some diastereomers, utilising (R)-(+)-pulegone as chiral source-material, and asymmetric dihydroxylation as a key step, are described.