329362-90-5Relevant academic research and scientific papers
Step-economic synthesis of (+)-crocacin C: A concise crotylboronation/[3,3] -sigmatropic rearrangement approach
Pasqua, Adele E.,Ferrari, Frank D.,Hamman, Chris,Liu, Yanzhou,Crawford, James J.,Marquez, Rodolfo
experimental part, p. 6989 - 6997 (2012/09/25)
The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.
Formal synthesis of (+)-crocacin C
Pasqua, Adele E.,Ferrari, Frank D.,Crawford, James J.,Marquez, Rodolfo
scheme or table, p. 2114 - 2116 (2012/07/13)
The formal synthesis of (+)-crocacin C is reported. The approach described takes advantage of a highly regioselective epoxide cuprate addition and a diastereoselective Overman rearrangement. The synthesis is practical and amenable to scale up.
Total synthesis of (+)-crocacin C
Sirasani, Gopal,Paul, Tapas,Andrade, Rodrigo B.
scheme or table, 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.
Asymmetric total synthesis of the myxobacteria metabolites crocacins A-D
Feutrill, John T.,Lilly, Michael J.,White, Jonathan M.,Rizzacasa, Mark A.
, p. 4880 - 4895 (2008/09/21)
The total syntheses of crocacins A-D are described. The key steps were a syn-aldol reaction followed by anti-reduction to secure the stereotetrad and acylation of an ene- or dienecarbamate to form the enamide. Crown Copyright
Concise total synthesis of (+)-crocacin C
Sirasani, Gopal,Paul, Tapas,Andrade, Rodrigo B.
, p. 6386 - 6388 (2008/12/22)
(Chemical Equation Presented) The cytotoxic natural product (+)-crocacin C (1) has been synthesized in 10 linear steps from commercially available Evans' chiral propionimide in 5% overall yield (8 steps from Evans' chiral dipropionate synthon). No protect
A formal total synthesis of crocacin C
Yadav,Reddy, P. Venkatram,Chandraiah
, p. 145 - 148 (2007/10/03)
An efficient total synthesis of a potent antifungal and moderate cytotoxic agent crocacin C is described. The synthesis involves the generation of four contiguous stereogenic centres via desymmetrization of a meso bicyclic dihydrofuran using asymmetric hy
Stereoselective formal synthesis of crocacin C via prins cyclization
Yadav,Sridhar Reddy,Purushothama Rao,Prasad
, p. 2049 - 2052 (2008/02/09)
A formal synthesis of crocacin C is described proving the versatility of Prins cyclization in natural product synthesis. The approach is convergent and highly stereoselective. Cross-metathesis and Heck reactions were utilized for the insertion of an aroma
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
Chakraborty, Tushar K,Jayaprakash, Sarva,Laxman, Pasunoori
, p. 9461 - 9467 (2007/10/03)
The total synthesis of potent antifungal and cytotoxic agent (+)-crocacin C in optically pure form following a convergent strategy is described here in detail. The synthesis also established the absolute stereochemistry of the molecule having a (6S,7S,8R,9S) configuration. While C8 and C9 stereocenters were built following a Ti(IV)-mediated diastereoselective 'non-Evans' aldol reaction based on 2-oxazolidinethione chiral auxiliary, lithium dimethylcuprate opening of a C6-C7 chiral epoxide prepared by Sharpless epoxidation method established the remaining two stereocentres.
Total synthesis of (+)-crocacin C
Chakraborty, Tushar K.,Jayaprakash, Sarva
, p. 497 - 499 (2007/10/03)
The first synthesis of (+)-crocacin C (3) in optically pure form is achieved following a convergent strategy. The synthesis also establishes the absolute stereochemistries of this novel class of potent antifungal and highly cytotoxic compounds. The naturally occurring crocacin C has (6S,7S,8R,9S) configuration, which is also the same for other congeners of the family, crocacins A, B and D.
