Lituarine synthetic studies. An efficient, stereocontrolled construction of the common c(7-19) tricyclic spiroketal fragment.
A highly efficient, stereocontrolled synthesis of (+)-4, the common C(7-19) tricyclic spiroketal fragment of the lituarines A, B, and C (1-3), has been achieved. Highlights of the synthesis include a remarkably facile 6-endo cyclization to access the C(8-12) pyran ring and a kinetically controlled acid-catalyzed spiroketalization. [reaction: see text]
Smith
A B
AB
Department of Chemistry, Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu
Frohn
M
M
D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D013141:Spiro Compounds; C442895:lituarine A; C442897:lituarine B; C442896:lituarine C