A Diels–Alder Approach to a Communesin Model: A/B‐Cyclization Route. Issue 16 (17th March 2015)

• Record Type: Journal Article
• Authors: Sanzone, Angelo; Somfai, Peter
• Is Part Of: European journal of organic chemistry. Issue 16(2015)
• Page Start: 3441
• Page End: 3449
• Publication Date: 2015-03-17
• Subjects: Synthesis design -- Cyclization -- Natural products -- Alkaloids -- Polycycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500177
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Compound3, a model system for communesin F, was approached by using a Diels–Alder reaction for the introduction of the vicinal quaternary stereocentres. Subsequent introduction of A/B‐ring system followed by D/E‐ring closure gave hexacyclic system22 . All attempts to reduce this material to give compound3 were, however, unproductive. Abstract : Compound3, a model system for communesin F, was approached by using a Diels–Alder reaction for the introduction of the vicinal quaternary stereocentres. All six rings were introduced, although it was not possible to achieve the required bis‐aminal oxidation state.