title: Synthesis of the ABC ring system of azaspiracid. 1. Effect of D ring truncation on bis-spirocyclization.
abstract: [reaction: see text] Synthesis of a spirocyclization precursor with a truncated D ring has been accomplished. Subsequent bis-spirocyclization induced the formation of equal amounts of the natural transoidal 10R,13R bis-spirocycle and its cisoidal 10R,13S epimer under an apparent thermodynamically controlled process.
authors.affiliation: Department of Chemistry and Biochemistry, University of Mississippi, University, Mississippi 38677, USA. rich.carter@oregonstate.edu
authors.forename: Rich G
authors.initials: RG
authors.lastname: Carter
authors.forename: T Campbell
authors.initials: TC
authors.lastname: Bourland
authors.forename: David E
authors.initials: DE
authors.lastname: Graves
mesh_terms: D000818:Animals; D049872:Bivalvia / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D008387:Marine Toxins; D013141:Spiro Compounds; C406592:azaspiracid; D000095702:Polyether Toxins