Synthesis of the cyclobutanone core of solanoeclepin A intramolecular allene butenolide photocycloaddition.
The compact tricyclic substructure of solanoeclepin A containing the cyclobutanone ring was prepared by using as the key step a highly regioselective intramolecular [2 + 2]-photocycloaddition reaction between one of the [small pi]-bonds of an allene and the CC double bond of a butenolide.
Hue
Bui T B
BT
Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands.
Dijkink
Jan
J
Kuiper
Sanne
S
Larson
Kimberly K
KK
Guziec
Frank S
FS
Goubitz
Kees
K
Fraanje
Jan
J
Schenk
Henk
H
van Maarseveen
Jan H
JH
Hiemstra
Henk
H
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006586:Hexanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010777:Photochemistry; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D003503:Cyclobutanes; D005663:Furans; D006586:Hexanes; D007659:Ketones; C431673:solanoeclepin A; C004511:butenolide; D015107:4-Butyrolactone