890409-89-9Relevant academic research and scientific papers
Total synthesis of (+)-crocacin C
Sirasani, Gopal,Paul, Tapas,Andrade, Rodrigo B.
experimental part, p. 3648 - 3655 (2010/08/03)
Two approaches toward the total synthesis of cytotoxic polyketide natural product (+)-crocacin C (1) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans' chiral propionimide (5% overall yield). No protecting groups were utilized in the total synthesis of 1.
Formal total syntheses of crocacin A-D
Besev, Magnus,Brehm, Christof,Fuerstner, Alois
, p. 1696 - 1708 (2007/10/03)
A concise route to the common polyketide fragment 5 of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features a syn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzed anti-selective addition of propargyl mesylate 10 to the chiral aldehyde 9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.
Total synthesis of (+)-crocacin D
Dias, Luiz C.,De Oliveira, Luciana G.,Vilcachagua, Janaina D.,Nigsch, Florian
, p. 2225 - 2234 (2007/10/03)
(Chemical Equation Presented) The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moie
Total synthesis of (+)-crocacin C
Dias, Luiz C.,De Oliveira, Luciana G.
, p. 3951 - 3953 (2007/10/03)
equation presented The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me2Cu
