Studies on the synthesis of pectenotoxin II: synthesis of a C(11)-C(26) fragment precursor via [3 + 2]-annulation reactions of chiral allylsilanes.
[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.
Micalizio
G C
GC
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Roush
W R
WR
D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
D005663:Furans; D018942:Macrolides; D011714:Pyrans; C098380:pectenotoxin 2; D000095702:Polyether Toxins