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endo, exo, syn, anti

Descriptors of the relative orientation of groups attached to non-bridgehead atoms in a bicyclo[x.y.z]alkane (xy > z > 0).
If the group is orientated towards the highest numbered bridge (zbridge, e.g. C-7 in example below) it is given the description exo; if it is orientated away from the highest numbered bridge it is given the description endo. If the group is attached to the highest numbered bridge and is orientated towards the lowest numbered bridge (xbridge, e.g. C-2 in example below) it is given the description syn; if the group is orientated away from the lowest numbered bridge it is given the description anti.
See also: syn, anti
PAC, 1996, 68, 2193 (Basic terminology of stereochemistry (IUPAC Recommendations 1996)) on page 2207
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8.
Last update: 2014-02-24; version: 2.3.3.
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