ISSN:
0947-3440
Keywords:
1,4-cis-Diaminotetra(di)deoxyheptitols
;
Tropa-type heterocycles
;
Total syntheses
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthetic potential of the dianhydrocycloheptenepentols 3 and dianhydrocycloheptaneheptols 4 - ultimately available from tropilidene - as intermediates en route to 1,4-cis-diaminotetra(di)deoxyheptitols is studied. With standard bivalent N nucleophiles (methyl-, benzylamine, hydrazines) the regioselective installation of two (e.g. 9, 34) amino functions has to compete with the generation of variously functionalized tropa-type 8-azabicyclo[3.2.1]octanes (e.g. 29, 30, 35, 45, 47). With azide (N3-) as monovalent nucleophile in unsaturated diepoxides 3 twofold, nearly regiospecific substitution (7) - in competition with [3,3]-sigmatropic migration (SN2′ substitution) -, in saturated diepoxides 4 regioselective monosubstitution (39) can be achieved.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970727
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