156767-44-1Relevant articles and documents
"One-pot" reductive lactone alkylation provides a concise asymmetric synthesis of chiral isoprenoid targets
Cao, Jia,Perlmutter, Patrick
supporting information, p. 4327 - 4329 (2013/09/24)
An efficient method, based on nucleophilic addition to lactones followed by modified in situ Clemmensen reduction, provides a short synthetic route to chiral isoprenoid targets. The efficacy of this method has been exemplified through the synthesis of several targets including the commercial fragrance Rosaphen, the side chain of Zaragozic acid C, the cotton leaf sex pheromone, and the side chains of vitamin E.
An alternative stereoselective synthesis of (R)- and (S)-Rosaphen via asymmetric catalytic hydrogenation
Matteoli, Ugo,Beghetto, Valentina,Scrivanti, Alberto,Aversa, Manuela,Bertoldini, Matteo,Bovo, Sara
experimental part, p. 779 - 783 (2012/02/05)
We report an alternative synthesis of the two enantiomers of the floral fragrance Rosaphen. The key intermediate 2-methyl-5-phenylpentanoic acid 3 is synthesized via asymmetric hydrogenation (ee up to 99%) in the presence of an in situ prepared ruthenium
Lipase-mediated preparation of optically active isomers of Rosaphen
Kawasaki, Masashi,Toyooka, Naoki,Saka, Tomoki,Goto, Michimasa,Matsuya, Yuji,Kometani, Tadashi
experimental part, p. 135 - 142 (2010/12/20)
The optically active isomers of Rosaphen (RS)-1 were synthesized from the chiral intermediate prepared by lipase-catalyzed desymmetrization of prochiral diol. The results of an olfactory evaluation of the prepared isomers are reported.
Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: Stereoconvergent suzuki reactions of racemic acylated halohydrins
Owston, Nathan A.,Fu, Gregory C.
supporting information; experimental part, p. 11908 - 11909 (2010/11/04)
A method for asymmetric alkyl-alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with alkylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.
Diastereoselective protonation of dienols: A formal approach to zaragozic acid C side chain
Comesse, Sebastien,Piva, Olivier
, p. 1061 - 1067 (2007/10/03)
The 2-methyl 5-phenylpropanal precursor of the side chain of zaragozic acid C has been prepared in 83% ee through the diastereoselective protonation of a photodienol generated in situ by irradiation of an α,β-unsaturated ester, bearing, as a chiral moiety