INOC REACTION IN ALKALOID SYNTHESIS - STEREOCONTROLLED FORMAL TOTAL SYNTHESIS OF (-PUMILIOTOXIN-C())

Authors
TOYOTA M ASOH T FUKUMOTO K
Citation
M. Toyota et al., INOC REACTION IN ALKALOID SYNTHESIS - STEREOCONTROLLED FORMAL TOTAL SYNTHESIS OF (-PUMILIOTOXIN-C()), Heterocycles, 45(1), 1997, pp. 147-156
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
1
Year of publication
1997
Pages
147 - 156
Database
ISI
SICI code
0385-5414(1997)45:1<147:IRIAS->2.0.ZU;2-Z
Abstract
A formal total synthesis of (+)-pumiliotoxin C (1), the antipode of th e arrow poison frog toxin, starting from the chirally homogeneous (1'S , 6'S)-2-(6'-benzyloxymethyl-2'-cyclohexyl)ethanol (2) is described. T he synthesis features the intramolecular nitrile oxide cycloaddition ( INOC) reaction of the nitro olefin (5) to furnish the isoxazoline (6).