title: Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.
abstract: [see reaction]. A synthesis of tetracycle 2 corresponding to the C(11)-C(26) fragment of pectenotoxin II is described. The synthesis features two highly stereoselective [3 + 2]-annulation reactions of chiral allylsilanes, generated via allylboration of aldehydes with the chiral gamma-silylallylborane 4 or the gamma-silylallylboronate 19, for construction of the highly substituted C and E rings.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
authors.forename: G C
authors.initials: GC
authors.lastname: Micalizio
authors.forename: W R
authors.initials: WR
authors.lastname: Roush
mesh_terms: D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D005663:Furans; D018942:Macrolides; D011714:Pyrans; C098380:pectenotoxin 2; D000095702:Polyether Toxins