A distinctive transformation based diversity oriented synthesis of small ring carbocycles and heterocycles from biocatalytically derived enantiopure α-substituted-β-hydroxyesters. Issue 14 (23rd March 2018)

• Record Type: Journal Article
• Authors: Halder, Joydev; Das, Debabrata; Nanda, Samik
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 14(2018)
• Page Start: 2549
• Page End: 2575
• Publication Date: 2018-03-23
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00233a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A series of structurally novel small ring carbocyclic and heterocyclic molecules were accessed in an enantiopure fashion. Abstract : A series of structurally novel small ring carbocyclic and heterocyclic molecules were accessed in an enantiopure fashion. The starting materials, α-substituted-β-hydroxyesters, were achieved through the biocatalytic dynamic kinetic resolution of parent β-ketoesters in an excellent enantio and diastereocontrolled way. The active functional groups present in the starting precursor, were then tuned sequentially through certain key transformations (functional group interconversions; FGIs) to yield several small molecular scaffolds in a diverse way. Specific transformations such as halocyclization, ene–yne metathesis, dipolar cycloaddition, Mitsunobu cyclization, ring closing metathesis and Pauson–Khand reactions were mainly applied to generate the diversity.