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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):
(a) Two of the six-membered rings are represented in chair conformations. Is the connection between these two rings analogous to that in cis- or trans-decalin?
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Based on our data, we think this problem is relevant for Professor Forbes' class at USOUTHAL.
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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.