198641-95-1

Upstream product

• 251115-98-7 (S)-3-Methyl-6-(toluene-4-sulfonyloxy)-hexanoic acid methyl ester 
• 251115-97-6 (S)-5-(3,3-Dimethyl-oxiranyl)-3-methyl-pentanoic acid methyl ester 
• 198641-92-8 methyl (S)-6-iodo-3-methylhexanoate 
• 198641-93-9 methyl (S)-3-methyl-7-octynoate 
• 158661-84-8 methyl (S)-6-hydroxy-3-methylhexanoate 
• 56994-89-9 (S)-(-)-citronellic acid,methyl ester 
• 2111-53-7 (S)-(-)-citronellic acid 
• 5949-05-3 (S)-Citronellal 
• 198641-94-0 methyl (3S)-3-methyl-2-phenylselenenyl-7-octynoate 

Downstream Products

• 141262-39-7 (3aS,8S,8bR,2'R)-3-[(E)-2',5'-dihydro-4'-methyl-5'-oxo-2'-furanyloxymethylene]-8-methyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one 
• 141262-39-7 (3aS,8S,8bR,2'S)-3-[(E)-2',5'-dihydro-4'-methyl-5'-oxo-2'-furanyloxymethylene]-8-methyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one 
• 141262-39-7 sorgolactone 
• 141262-39-7 (3aR,8S,8bS,2'S)-3-[(E)-2',5'-dihydro-4'-methyl-5'-oxo-2'-furanyloxymethylene]-8-methyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one 
• 198641-96-2 (S)-2-Bromomethyl-6-methyl-cyclohex-1-enecarboxylic acid methyl ester 
• 251115-99-8 methyl (6S)-2-bromo-2-bromomethyl-6-methylenecyclohexane-1-carboxylate 

Relevant academic research and scientific papers

Plant bioregulators, 2. Syntheses of (±)- and (+)-sorgolactone, the germination stimulant from Sorghum bicolor

Syntheses of (±)-2a, the racemate of the structure proposed for sorgolactone, and its three racemic stereoisomers have been accomplished with confirmation of the stereostructures of the intermediate (±)-10 and the final product (±)-2a by X-ray analysis. Its optically active form, (3aR,8S,8bS,2'R)-(+)-2a, has also been prepared from (S)-(-)-citronellal by employing radical cyclization of 18 to 19 as the key step. Spectroscopic properties of the synthetic products are compared with those reported for natural sorgolactone. Bioassays using clover broomrape (Orobanche minor) seeds have revealed that all the stereoisomers strongly stimulate their germination.

Synthesis of (3aR,8S,8bS,2'R)-(+)-sorgolactone and its stereoisomers, the germination stimulant from sorghum bicolor

Methyl (S)-citronellate (2) was converted to (3aR,8S,8bS,2'R)-(+)- sorgolactone (1a) by employing the radical cyclization of 6 to 7 as the key- step. Three other stereoisomers (1b, 1c and 1d) of sorgolactone were also prepared. The CD spectrum of la was in accord with that reported for the natural product.