title: Synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1: an iodoetherification-dehydroiodination strategy for complex spiroketals.
abstract: An unusual spiroketalization strategy in which a hydroxyalkene serves as a precursor to a cyclic enol ether was applied to the synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1. The trioxadispiroketal product, which represents a double anomeric effect, was obtained as a single trioxadispiroketal diastereomer. A key ploy in the synthesis of the CD segment was the use of a cyclopropane as a synthon for the C-14 methyl group.
authors: Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10065, USA.
authors: Xiaohua
authors: X
authors: Li
authors: Jialiang
authors: J
authors: Li
authors: David R
authors: DR
authors: Mootoo
mesh_terms: D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D000095702:Polyether Toxins
chemical_list: D005663:Furans; D006847:Hydrocarbons, Iodinated; D008387:Marine Toxins; D013141:Spiro Compounds; C406592:azaspiracid; D000095702:Polyether Toxins; C520774:spiroketal