Synthesis of the C11-C29 fragment of amphidinolide F.
[reaction: see text] An efficient synthesis of the C(11)-C(29) fragment 31 of amphidinolide F has been accomplished via a diastereoselective [3 + 2]-annulation reaction of allylsilane 5 and ethyl glyoxylate to prepare the key tetrahydrofuran 15 and a highly stereoselective methyl ketone aldol reaction to generate the C(11)-C(16) segment.
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
J Brad
JB
Shotwell
William R
WR
Roush
D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides; D000097442:Amphidinolides
D006571:Heterocyclic Compounds; D018942:Macrolides; C072156:amphidinolide F; D000097442:Amphidinolides