Total Synthesis of a 6, 6‐Spiroketal Metabolite, Dinemasone A. Issue 3 (27th November 2012)

• Record Type: Journal Article
• Authors: Raji Reddy, Chada; Srikanth, Boinapally; Dilipkumar, Uredi; Rao, Kakita Veera Mohana; Jagadeesh, Bharatam
• Is Part Of: European journal of organic chemistry. Issue 3(2013)
• Page Start: 525
• Page End: 532
• Publication Date: 2012-11-27
• Subjects: Total synthesis -- Asymmetric synthesis -- Natural products -- Spiro compounds -- Michael addition; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201246
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The stereoselective total synthesis of dinemasone A has been accomplished. The key reactions, Sharpless asymmetric epoxidation, lithium‐mediated epoxy alcohol opening, and double‐intramolecular hetero‐Michael addition, gave access to dinemasone A from lactic acid esters. The stereochemistry at the spiro carbon was determined using extensive NMR studies. Abstract : The stereoselective total synthesis of dinemasone A was accomplished in a longest linear sequence of 14 steps using double‐intramolecular hetero‐Michael addition as the key spiroketalisation reaction.