71968-02-0Relevant articles and documents
Total Synthesis of Asperchalasines A, D, E, and H
Long, Xianwen,Ding, Yiming,Deng, Jun
, p. 14221 - 14224 (2018)
The first total syntheses of the cytochalasan dimers asperchalasines A, D, E, and H have been accomplished. The key steps of the synthesis include a highly stereoselective intermolecular Diels–Alder reaction and a Horner–Wadsworth–Emmons macrocyclization to establish the key monomer aspochalasin B, and an intermolecular Diels–Alder reaction followed by a biomimetic oxidative heterodimerization by 5+2 cycloaddition to furnish asperchalasine A. The synthetic efforts provide insight into the biosynthetic pathway of cytochalasan dimers and enables the further study of their biological properties.
Biomimetic Synthesis of (+)-Aspergillin PZ
Reyes, Julius R.,Winter, Nils,Spessert, Lukas,Trauner, Dirk
, p. 15587 - 15591 (2018/11/21)
The cytochalasans are a large family of polyketide natural products with potent bioactivities. Amongst them, the aspochalasins show particularly intricate and fascinating structures. To gain insight into their structural diversity and innate reactivity, we have developed a rapid synthesis of aspochalasin D, the central member of the family. It proceeded in 13 steps starting from divinyl carbinol and utilized a high pressure Diels–Alder reaction that features high regio- and stereoselectivity. So far, our work has culminated in a biomimetic synthesis of aspergillin PZ, an intricate pentacyclic aspochalasan.
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
