One-Pot Stereoselective Double Intramolecular Oxymercuration: Synthesis of Four Isomers of an Unsymmetrical Bis-Tetrahydrofuran Ring System

• Published in: European Journal of Organic Chemistry Vol. 2010; no. 32; pp. 6263 - 6268
• Main Authors: Mohapatra, Debendra K., Naidu, P. Ramesh, Reddy, D. Srinivas, Nayak, Sabita, Mohapatra, Seetaram
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.11.2010; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Mercury; Natural products; Organic chemistry; Oxygen heterocycles; Physical Sciences; Preparations and properties; Science & Technology; Stereoselectivity; Toxicity; Oxygen heterocycles; Toxicity; MODE; BULLATACIN; ANNONACEOUS ACETOGENINS; ANTITUMOR; Stereoselectivity; CHAIN; INHIBITION; Natural products; CHEMISTRY; FRAGMENT; Mercury; CYCLIZATION; Intramolecular reaction; One pot reaction; Hydroxylation; Furan derivatives; Asymmetric molecule; Natural compound; Oxygen heterocycle; Tetrahydrofurane; Biological activity; Polyketide; Oxymercuration; Acetogenin; Chemical synthesis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201000861

Stereoselective one‐pot double intramolecular oxymercuration has been demonstrated to be the key reaction in the efficient preparation of the mono‐hydroxylated bis‐tetrahydrofuran ring system present in asimitrin and salzmanolin, two naturally occurring biologically active nonclassical acetogenins. An efficient preparation of a mono‐hydroxylated bis‐tetrahydrofuran ring system present in asimitrin and salzmanolin, two naturally occurring biologically active nonclassical acetogenins, has been achieved by a one‐pot stereoselective double intramolecular oxymercuration as the key reaction.