A biosynthetic pathway was recently proposed for the polycyclic, cytotoxic compound aspernomine, isolated from the fungus Aspergillus nomius (J. Am. Chem. Soc. 2012, 134, 8078–8081):
(d) Consider the six-carbon acyclic substituent bound to one of the bridgehead carbons. What is its relationship (axial or equatorial) to each of the chairs?
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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.