Progress toward the total synthesis of frondosin C.
A straightforward approach toward the total synthesis of frondosin C is described. This strategy involves a key one-pot, microwave-assisted 5-exo cyclization-Claisen rearrangement sequence that was used for the expedient assembly of the frondosic C scaffold. Subsequent manipulation of the tetracyclic core allowed the synthesis of an advanced intermediate bearing the characteristic diene moiety in the B ring. [reaction: see text]
Li
Xin
X
Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, CT 06320, USA.
Kyne
Robert E
RE
Ovaska
Timo V
TV
D000818:Animals; D002384:Catalysis; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry
D006576:Heterocyclic Compounds, 4 or More Rings; C506349:frondosin C