Diastereoselective synthesis of the C(17)-C(28) fragment (the C-D spiroketal unit) of spongistatin 1 (altohyrtin A) via a kinetically controlled iodo-spiroketalization reaction.
[reaction: see text] A convergent and stereocontrolled synthesis of spiroketal 15 corresponding to the C-D fragment of spongistatin 1 has been accomplished by a sequence utilizing a kinetically controlled intramolecular iodo-spiroketalization of glycal 2, which in turn was synthesized via a ring-closing metathesis reaction.
Holson
Edward B
EB
Department of Chemistry, University of Michigan, 930 North University, Ann Arbor, Michigan 48109, USA.
Roush
William R
WR
D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D013237:Stereoisomerism; D000095702:Polyether Toxins
D004988:Ethers, Cyclic; D007783:Lactones; D018942:Macrolides; C083856:spongistatin 1; D000095702:Polyether Toxins