Journal
SYNTHESIS-STUTTGART
Volume 47, Issue 17, Pages 2497-2522Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1378863
Keywords
alpha-heteraspiranes; chirons; stereoselective syntheses; spiroannulations; spirocyclic amino acids; spirocyclic nucleosides
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The biological importance and wide occurrence of spirane systems in nature have stimulated studies in spirane chemistry. The fundamental spirane framework consists of two monocyclic rings linked in an orthogonal relationship by a common ring carbon. This review covers families of annular -monoheteraspiranes starting with -heteraspiro[2.4]heptanes and terminating with -hetera[5.6]dodecanes; the annular heteroatoms are N, O, or S. The spirane systems are arranged according to the relative size of the two monocyclic rings with highest priority for the smaller ring, Often optically active spiranes are prepared for biological reasons by chemical modifications of natural products related to the spirane to be prepared. Chiral auxiliaries are useful in the introduction and control of stereochemistry in the construction of spiranes as intermediates in the preparation of novel amino acids and nucleosides. Another aspect of chiral spirane chemistry concerns modifications and conformational restrictions introduced in natural carbohydrates, nucleosides, and amino acids. 1 Introduction 2 Heteraspira[2.m]alkanes 3 Heteraspira[3.m]alkanes 4 Heteraspira[4.m]alkanes 5 Heteraspira[5.m]alkanes
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