124575-36-6Relevant academic research and scientific papers
Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins and Formal Synthesis of Trichoderone A
Gayraud, Oscar,Laroche, Benjamin,Casaretto, Nicolas,Nay, Bastien
, p. 5755 - 5760 (2021)
Aspochalasins are leucine-derived cytochalasins. Their complexity is associated with a high degree of biosynthetic oxidation, herein inspiring a two-phase strategy in total synthesis. We thus describe the synthesis of a putative biomimetic tetracyclic int
First Total Synthesis, Structure Revision, and Natural History of the Smallest Cytochalasin: (+)-Periconiasin G
Zaghouani, Mehdi,Kunz, Caroline,Guédon, Laura,Blanchard, Florent,Nay, Bastien
, p. 15257 - 15260 (2016)
The total synthesis of the smallest cytochalasin isolated so far, periconiasin G, which bears a seven-membered ring in lieu of the usual macrocycle, has been performed from both enantiomers of citronellal, relying on an intramolecular Diels–Alder reaction in favor of the natural endo stereochemistry. We show that, among the four synthesized stereoisomers, including the exo isomers, the one matching the NMR data of the natural product was not that assigned in the original report, imposing structure revision. The natural product, previously isolated from a plant-mutualistic fungus, was biologically investigated taking into account its natural history, showing significant effects against the phytopathogenic fungus Botrytis cinerea and thus opening new opportunities in combating this pest.
Identification of an unexpected 2-oxonia[3,3]sigmatropic rearrangement/aldol pathway in the formation of oxacyclic rings. Total synthesis of (+)-aspergillin PZ
Canham, Stephen M.,Overman, Larry E.,Tanis, Paul S.
supporting information; experimental part, p. 9837 - 9843 (2012/02/14)
This paper reports the first unambiguous evidence that the cascade synthesis of tetrahydrofuran-containing oxacyclic molecules depicted in Scheme 12 can take place by a 2-oxonia[3,3]sigmatropic/aldol mechanism rather than by a Prins cyclization/pinacol rearrangement sequence. The 8-oxabicyclo[3.2.1]octyl aldehyde products of this reaction, 20 and 29, were employed to complete the first total synthesis of the structurally remarkable isoindolone alkaloid (+)-aspergillin PZ (1). The lack of activity seen in two tumor cell lines for synthetic (+)-aspergillin PZ calls into question the suggestion that aspergillin PZ, like many aspochalasin diterpenes, might exhibit useful antitumor properties.
CYTOCHALASAN SYNTHESIS: SYNTHESIS OF (17S,18S)-17,18-DIHYDROXY-10-(PROP-2-YL)-14-METHYL-CYTOCHALASA-6(7),13Z,19E-TRIENE-1,21-DIONE; AN ISOMER OF ASPOCHALASIN C
Craven, Andrew P.,Dyke, Hazel J.,Thomas, Eric J.
, p. 2417 - 2430 (2007/10/02)
On heating a dilute solution of a 2:1 mixture of the (8'E)- and (8'Z)-3-(1-oxotrienyl)-Δ3-pyrrolin-2-ones (36), Diels Alder cyclization occured.The minor (8'Z)-pyrrolinone cyclized stereoselectively to give the endo adduct (39) which has the as
