Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.

ABSTRACT: A unified enantioselective total synthesis and anticancer evaluation of all known epoxide-containing communesin alkaloids and related derivatives is described. Our synthesis is predicated on the convergent and modular diazene-directed assembly of two complex fragments to secure the critical C3a-C3a' linkage followed by a guided biomimetic aminal reorganization to deliver the heptacyclic core of these alkaloids. Concise enantioselective syntheses of the fragments were devised, with highlights including the application of a rationally designed sulfinamide chiral auxiliary, an efficient calcium trifluoromethanesulfonate promoted intramolecular amination, and a diastereoselective epoxidation that simultaneously converts the new chiral auxiliary to a versatile amine protective group. The modula

SUBMITTER: Pompeo MM 

PROVIDER: S-EPMC6743222 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature