51704-29-1Relevant articles and documents
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
Rhodium-catalyzed olefin isomerization/allyl claisen rearrangement/ intramolecular hydroacylation cascade
Okamoto, Ryuichi,Tanaka, Ken
supporting information, p. 2112 - 2115 (2013/06/05)
It has been established that a cationic Rh(I)/dppf complex catalyzes the olefin isomerization/allyl Claisen rearrangement/intramolecular hydroacylation cascade of di(allyl) ethers to produce substituted cyclopentanones in good yields under mild conditions.
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
scheme or table, 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.
Cyclopropyl methyl bromide-mediated gem-diallylation: Total synthesis of (±)-α-cuparenone
Shivakumar,Salunke, Ganesh B.,Kumar, Suneel
experimental part, p. 1952 - 1957 (2011/06/26)
The total synthesis of (±)-α-cuparenone, an aromatic sesquiterpene, has been described using the radical mediated gem-diallylation of substituted cyclopropyl methylbromide followed by ring-closing metathesis approach.
A facile total synthesis of (±)-α-cuparenone employing diallylation and RCM as key steps
Chavan, Subhash P.,Dhawane, Abasaheb N.,Kalkote, Uttam R.
, p. 965 - 966 (2008/02/04)
A short and concise total synthesis of α-cuparenone employing one-pot diallylation and RCM as the key steps is 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 (+)-
