Synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1: an iodoetherification-dehydroiodination strategy for complex spiroketals.
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.
Li
Xiaohua
X
Department of Chemistry, Hunter College, 695 Park Avenue, New York, New York 10065, USA.
Li
Jialiang
J
Mootoo
David R
DR
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
D005663:Furans; D006847:Hydrocarbons, Iodinated; D008387:Marine Toxins; D013141:Spiro Compounds; C406592:azaspiracid; D000095702:Polyether Toxins; C520774:spiroketal