37519-97-4Relevant articles and documents
Enantioselective access to (-)-Ambrox starting from β-farnesene
Chapuis, Christian
, p. 197 - 214 (2014)
Starting from inexpensive (E)-β-farnesene (1), an eight-step enantioselective synthesis of the olfactively precious Ambrox ((-)-2a) has been performed. The crucial step is the catalytic asymmetric isomerization of (2E,6E)-N,N-diethylfarnesylamine (3) to t
Frogolide – An Unprecedented Sesquiterpene Macrolactone from Scent Glands of African Frogs
Menke, Markus,Melnik, Kristina,Peram, Pardha S.,Starnberger, Iris,H?dl, Walter,Vences, Miguel,Schulz, Stefan
, p. 2651 - 2656 (2018/03/29)
Some amphibians use chemical signals in addition to optical and acoustical signals to transmit information. Males of mantellid frogs from Madagascar and hyperoliid frogs from Africa emit complex, species- and sex-specific bouquets of volatiles from their femoral or gular glands. We report here on the identification, synthesis, and determination of the absolute configuration of a macrocyclic lactone occurring in several species of both families, (S)-3,7,11-dodec-6,10-dien-12-olide (S-14, frogolide). Macrolides are a preferred compound class of frog volatiles. Nevertheless, frogolide is the first macrocyclic lactone obviously derived from the terpene pathway, in contrast to known frog macrolides that are usually formed via the fatty acid biosynthetic pathway.
METHOD FOR PRODUCING OPTICALLY ACTIVE 2,3-DIHYDROFARNESAL
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, (2017/07/08)
PROBLEM TO BE SOLVED: To provide a synthetic intermediate useful for obtaining optically active 2,3-dihydrofarnesal high in chemical purity and optical purity, and a satisfactorily efficient method for producing the intermediate. SOLUTION: Provided is optically active farnesyl enamine represented by formula (4) (*denotes an asymmetric carbon atom; R1 and R2 respectively independently denote H, a substituted/unsubstituted 1-20C alkyl group, a substituted/unsubstituted 3-8 membered-ring alicyclic group, a substituted/unsubstituted 6-15C aryl group; a substituted/unsubstituted 2-15C heterocyclic group or a substituted/unsubstituted 7-12C aralkyl group; and R1 and R2 are not simultaneously H or R1 and R2 may be coupled to form a ring). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT