Stereoselective Synthesis of the DE Ring Portion of Kadcoccilactone A by a Radical Addition/Cyclization Approach. Issue 45 (1st December 2022)

• Record Type: Journal Article
• Authors: Noguchi, Kimihiro; Saito, Sayuri; Yamakoshi, Hiroyuki; Nakamura, Seiichi
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 45(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-01
• Subjects: Allyl sulfide -- Cascade reaction -- Intramolecular alkylation -- Photocatalytic reaction -- Schinortriterpenoids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201201
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A stereoselective synthesis of the DE ring portion of kadcoccilactone A, triterpenoid isolated from Kadsura coccinea, has been achieved starting from a chiral building block, utilizing a photocatalytic decarboxylative addition/cyclization/fragmentation sequence to construct the five‐membered ring and intramolecular alkylation to create the quaternary stereocenter as key steps. Abstract : Photocatalytic decarboxylative addition/cyclization/fragmentation sequence can be employed for the stereoselective construction of the hydrindan skeleton of kadcoccilactone A. The tricyclic product could be transformed to the DE ring fragment having three contiguous quaternary stereocenters in an eight‐step sequence involving an intramolecular alkylation. Phth=phthaloyl, TBS= tert ‐butyldimethylsilyl, bpy=bipyridine.