Efficient synthesis of the C(7)-C(20) subunit of amphidinolides C and F.
Synthesis of the C(7)-C(20) subunit of amphidinolides C and F has been accomplished utilizing a Me(3)Al-mediated ring opening of a vinyl iodide/allylic epoxide to establish the C(12,13)anti stereochemistry, an organolithium coupling/olefination sequence to construct the C(9)-C(11) diene moiety and a sulfone alkylation/hydroxylation strategy to join the C(7)-C(14) and C(15)-C(20) fragments.
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR 97331, USA.
Subham
S
Mahapatra
Rich G
RG
Carter
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D000097442:Amphidinolides
D000577:Amides; D018942:Macrolides; C429132:amphidinolide C; D000097442:Amphidinolides; C072156:amphidinolide F