title: Synthesis of the ABC ring system of Azaspiracid. 2. A systematic study into the effect of C(16) and C(17) substitution on bis-spirocyclization.
abstract: [reaction: see text] A systematic study into the effect of C(16) and C(17) substitution on the stereochemical outcome of bis-spirocyclization to form the ABC ring system of azaspiracid is disclosed. Successful construction of the natural 10R,13R bis-spirocyclic stereochemistry has been accomplished on the C(16) benzyloxy-containing precursor.
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: David E
authors.initials: DE
authors.lastname: Graves
authors.forename: Melissa A
authors.initials: MA
authors.lastname: Gronemeyer
authors.forename: Gregory S
authors.initials: GS
authors.lastname: Tschumper
mesh_terms: D000478:Alkylation; D000818:Animals; D049872:Bivalvia / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D000095702:Polyether Toxins
chemical_list: D008387:Marine Toxins; D013141:Spiro Compounds; C406592:azaspiracid; D000095702:Polyether Toxins