16196-32-0Relevant academic research and scientific papers
Asymmetric total synthesis of (R)-α-cuparenone, (S)-cuparene and formal synthesis of (R)-β-cuparenone through Meinwald rearrangement and ring closing metathesis (RCM) reaction
Kumar, Rajan,Halder, Joydev,Nanda, Samik
, p. 809 - 818 (2017/01/16)
Asymmetric synthesis of enantiopure cuparenoid sesquiterpenes (R)-α-cuparenone, (S)-cuparene and a formal synthesis of (R)-β-cuparenone was presented in this article. Meinwald rearrangement of an enantiopure trisubstituted 2,3-epoxy alcohol derivative was
Construction of an asymmetric quaternary carbon via an asymmetric aza-Claisen rearrangement and its application in the total synthesis of (+)-α-cuparenone
Nishii, Takeshi,Miyamae, Fumiaki,Yoshizuka, Makoto,Kaku, Hiroto,Horikawa, Mitsuyo,Inai, Makoto,Tsunoda, Tetsuto
, p. 739 - 741 (2012/09/05)
Excess lithium hexamethyldisilazide (LHMDS) with LiCl prompted the asymmetric aza-Claisen rearrangement of carboxamide and retarded the decomposition of its amide enolate. The addition of these two reagents was a key step that led to the total synthesis o
Palladium-catalyzed asymmetric quaternary stereocenter formation
Gottumukkala, Aditya L.,Matcha, Kiran,Lutz, Martin,De Vries, Johannes G.,Minnaard, Adriaan J.
experimental part, p. 6907 - 6914 (2012/07/01)
An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright
A chiral pool based approach to antipodes of α-cuparenone
Chavan, Subhash P.,Lasonkar, Pradeep B.
, p. 1496 - 1500,5 (2012/12/12)
A synthetic route to both antipodes of α-cuparenone was achieved from the readily available chiral pool starting material l-malic acid and involved cyclopentannulation as the key step.
A chiral pool based approach to antipodes of α-cuparenone
Chavan, Subhash P.,Lasonkar, Pradeep B.
, p. 1496 - 1500 (2013/01/15)
A synthetic route to both antipodes of α-cuparenone was achieved from the readily available chiral pool starting material l-malic acid and involved cyclopentannulation as the key step.
Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling
Zhang, Ping,Le, Hai,Kyne, Robert E.,Morken, James P.
supporting information; experimental part, p. 9716 - 9719 (2011/08/04)
The Pd-catalyzed cross-coupling of racemic tertiary allylic carbonates and allylboronates is described. This reaction generates all-carbon quaternary centers in a highly regioselective and enantioselective fashion. The outcome of these reactions is consistent with a process that proceeds by way of 3,3′-reductive elimination of bis(η1-allyl)palladium intermediates. Strategies for distinguishing the product alkenes and application to the synthesis of (+)-α-cuparenone are also described.
Parallel syntheses of (+)- and (-)-α-cuparenone by radical combination in crystalline solids
Natarajan, Arunkumar,Ng, Danny,Yang, Zhe,Garcia-Garibay, Miguel A.
, p. 6485 - 6487 (2008/09/17)
Photo[Organic]synthesis: Irradiation of well-designed crystalline ketones can result in the solvent-free generation of compounds having adjacent quaternary stereogenic centers, as illustrated for the enantiospecific synthesis of the natural products (+)-
A novel method for the asymmetric synthesis of 4,4-disubstituted 2-cyclopentenones from optically active 1-chlorovinyl p-tolyl sulfoxides and its application to the asymmetric total synthesis of (+)-α-cuparenone
Satoh, Tsuyoshi,Yoshida, Masaaki,Takahashi, Yasuhiro,Ota, Hiroyuki
, p. 281 - 288 (2007/10/03)
Enantiomerically pure 1-chlorovinyl p-tolyl sulfoxides having two different substituents at the 2-position were synthesized from unsymmetrical ketones and (R)-(-)-chloromethyl p-tolyl sulfoxide in three steps. Treatment of the 1-chlorovinyl p-tolyl sulfoxides with cyanomethyllithium at -78°C to room temperature gave optically active 2-amino-1-cyano-5,5-disubstituted-1,3-cyclopentadienes in high yields with very high asymmetric induction from the stereogenic center of the sulfoxide moiety. A mechanism for the asymmetric induction is proposed. The products were treated with phosphoric acid in acetic acid at reflux temperature to give enantiomerically pure 4,4-disubstituted 2-cyclopentenones in good yields. As an application of this synthetic method, a relatively short (seven steps) total asymmetric synthesis of (+)-α-cuparenone from methyl 4-methylphenyl ketone is described.
Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers Using Chiral Bicyclic Lactams and Diastereoselective Protonation. Asymmetric Synthesis of (+)-Laurene
Schwarz, Jacob B.,Meyers, A. I.
, p. 6511 - 6514 (2007/10/03)
The chiral bicyclic lactam 5, previously reported in the synthesis of (-)-α-cuparenone, was used to construct the more complex title compound 2.A mixture of cyclopentenones 8 and 9 was subjected to deprotonation/reprotonation to provide 8 in high diastereomeric excess.Transformation of 8 to the title compound was achieved by catalytic hydrogenation to 13, followed by methylenation with the Tebbe reagent.
A Concise and Enantioselective Approach to Cyclobutanones by Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols. An Enantiocontrolled Synthesis of (+)- and (-)-α-Cuparenones
Nemoto, Hideo,Ishibashi, Hiroki,Nagamochi, Masatoshi,Fukumoto, Keiichiro
, p. 1707 - 1712 (2007/10/02)
A tandem Katsuki-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alkyl(or 1-aryl)-1-(hydroxymethyl)cyclobutanones (3a-i) in high yields and high enantiomeric excess.These compounds are potentially valuable synthons for the enantioselective creation of the quaternary carbons.Hence, this enabled us to accomplish a concise and enantioselective total synthesis of both (+)- and (-)-cuparenones (11).
