406
2
General Synthetic Methods
This protocol can be applied to the 6-O-acetyl-5-enopyranoside 229 with good efficiency and the utility is well demonstrated by the synthesis of the D-myo-inositol phosphate,
IP3 [193,194].
Compound 231 is converted to the Ferrier product 232, the precursor of novel aminoglucosides [183] ( > Scheme 50). Carbocyclization of the glycoside 233 gives the cyclohexane 234,
from which tetrazoline analogs can be synthesized [195]. The Ferrier cyclization found new
utility in the synthetic chemistry of Amaryllidaceae alkaloids [196]. Thus, the glycoside 235
is transformed to the Ferrier-II product 236, the logical intermediate to 7-deoxypancratistatin.
A novel reductive carbocyclization of hex-5-enopyranosides retains the substituent at the
anomeric center and the ring oxygen remains as the new hydroxy group [197]. The stereo⊡ Scheme 51
⊡ Scheme 52
2
General Synthetic Methods
This protocol can be applied to the 6-O-acetyl-5-enopyranoside 229 with good efficiency and the utility is well demonstrated by the synthesis of the D-myo-inositol phosphate,
IP3 [193,194].
Compound 231 is converted to the Ferrier product 232, the precursor of novel aminoglucosides [183] ( > Scheme 50). Carbocyclization of the glycoside 233 gives the cyclohexane 234,
from which tetrazoline analogs can be synthesized [195]. The Ferrier cyclization found new
utility in the synthetic chemistry of Amaryllidaceae alkaloids [196]. Thus, the glycoside 235
is transformed to the Ferrier-II product 236, the logical intermediate to 7-deoxypancratistatin.
A novel reductive carbocyclization of hex-5-enopyranosides retains the substituent at the
anomeric center and the ring oxygen remains as the new hydroxy group [197]. The stereo⊡ Scheme 51
⊡ Scheme 52