Olefin metathesis-iodoetherification-dehydroiodination strategy for spiroketal subunits of polyether antibiotics.
The convergent synthesis of two pentacyclic analogues of the polyether monensin A is described. Although different with respect to the configuration of the alcohol at the 3 position of the six-membered ring of the spiroketal subunit, the configuration at the acetal center in both structures is unchanged and is consistent with the anomeric effect. The key synthetic steps are the coupling of two complex segments via an olefin metathesis, and the subsequent conversion of a dihydroxyalkene to the spiroketal through an iodoetherification-dehydroiodination sequence. The compatibility of these transformations with a variety of functional groups makes the overall strategy appropriate for highly substituted frameworks.
Tony
Kurissery A
KA
Department of Chemistry, Hunter College/CUNY, 695 Park Avenue, New York, New York 10021, USA.
Dabideen
Darrin
D
Li
Jialiang
J
Díaz-Hernández
Maria Dolores
MD
Jiménez-Barbero
Jesús
J
Mootoo
David R
DR
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D054879:Halogenation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008985:Monensin / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D004987:Ethers; D005663:Furans; D013141:Spiro Compounds; C520774:spiroketal; D008985:Monensin