22963-93-5Relevant academic research and scientific papers
A NEW SYNTHETIC ROUTE TO JUVENILE HORMONE KINETIC RESOLUTION OF EPOXIDES USING ORGANOALUMINUM REAGENT
Naruse, Yuji,Esaki, Toru,Yamamoto, Hisashi
, p. 1417 - 1420 (1988)
A short synthetic route to C16-juvenile hormone is described which depends on new oxirane ring opening methodology and which also involves the joining of intermediate 8 and 12 in a one flask operation to construct the sesquiterpene structure.
Enantioselective synthesis of juvenile hormone III in three steps from methyl farnesoate
Crispino,Sharpless
, p. 777 - 779 (1993)
The asymmetric dihydroxylation of methyl farnesoate resulted in regioselective dihydroxylation of the 10,11 olefin to give the (10S) and (10R)-(2E,6E)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoates in high ee. These diols were converted to juvenile hormone III and its enantiomer.
KINETIC RESOLUTION OF EPOXIDES BY CHIRAL ORGANOALUMINIUM CALTALYST SHORT SYNTHESIS OF (-)-C16 JUVENILE HORMONE
Naruse, Yuji,Esaki, Toru,Yamamoto,Hisashi
, p. 4747 - 4756 (2007/10/02)
The use of chiral organoaluminium reagent as a catalyst to resolve simple ketoepoxides is explored.The optically pure ketoepoxide 10 was recovered after 80percent conversion.The recovered pure epoxides is a useful chiral building block in the synthesis of
SYNTHESIS OF BOTH THE ENANTIOMERS OF JUVENILE HORMONE III
Mori, Kenji,Mori, Hideto
, p. 4097 - 4106 (2007/10/02)
Both the enantiomers (ca.100percent e.e.) of juvenile hormone III were synthesized employing (S)-3-hydroxy-2,2-dimethylcyclohexanone as a single chiral source.
