128926-36-3Relevant academic research and scientific papers
Novel synthesis of degradation products of carotenoids, megastigmatrienone analogues and blumenol-A
Ito, Nobuhiko,Etoh, Takeaki,Hagiwara, Hisahiro,Kato, Michiharu
, p. 1571 - 1579 (2007/10/03)
Synthesis of 4-alkylidene-3,5,5-trimethylcyclohex-2-enones 7 has been achieved utilising 1,4-conjugate dehydrobromination of allylic bromides 5 as a key step. This chemical transformation is applied to the synthesis of degradation products of carotenoids: megastigmatrienones 7e/1-4,4-methylene-3,5,5-trimethylcyclohex-2-enone 7a, 4-(3-hydroxybutylidene)-3,5,5-trimethylcyclohex-2-enone 9,1,3,7,7-tetramethyl-2-oxabicyclo[4.4.0]dec-5-en-9-one 10a-b and 3,4,7,8-tetrahydro-4,4,7-trimethylnaphthalen-2(6H)-one 15. A novel photoisomerisation of 4-[(Z)-3-acetoxybut-2-enyl]-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 19 to 4-[(E)-3-acetoxybut-2-enyl]-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 20 enables us to synthesise blumenol-A 21.
Structure-Odor Correlation, XIII. - Synthesis and Olfactive Properties of Megastigmatrienone Analogues
Weyerstahl, Peter,Meisel, Thomas,Mewes, Klaus,Negahdari, Shoreh
, p. 19 - 25 (2007/10/02)
The key compound 9 was readily prepared in larger quantities by an improvement of a known procedure.Addition of carbanions to the unprotected ketone 9 gives the hydroxy ketones 16 - 21 via the acetals 10 - 15.Dehydration of 16 - 20 furnishes the dienones
