Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers: convergent synthesis of the CDEFG-ring system.
[reaction: see text] A convergent synthetic route to the CDEFG-ring system of gambieric acids, potent antifungal polycyclic ether marine natural products, has been developed. The present synthesis features convergent union of the CD- and G-rings through esterification, formation of the E-ring as a lactone form, stereoselective allylation to set the C26 stereocenter, and ring-closing metathesis reaction to construct the nine-membered F-ring.
Sato
Kazushi
K
Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Tsutsumidori-Amamiya, Aoba-ku, Sendai 981-8555, Japan.
Sasaki
Makoto
M
D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis*; D002922:Ciguatoxins / Q000138:chemical synthesis*; D003500:Cyclization; D004141:Dinoflagellida / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D015394:Molecular Structure
D000935:Antifungal Agents; D004988:Ethers, Cyclic; D002922:Ciguatoxins; C080898:gambieric acid A; C080900:gambieric acid B