Problem

Multifidene is a sperm-cell-attracting substance released by the female of a species of br...

Multifidene is a sperm-cell-attracting substance released by the female of a species of brown algae. It has the constitution shown.

Assuming that the double bond in the five-membered ring of all of the isomers is cis:

(a) How many stereoisomers are represented by this constitution?


(b) If the substituents on the five-membered ring are cis to each other, how many stereoisomers are represented by this constitution?


(c) If the butenyl side chain has the Z configuration of its double bond, how many stereoisomers are possible?


(d) Draw stereochemically accurate representations of all the stereoisomers that satisfy the structural requirements just described.


(e) How are these stereoisomers related? Are they enantiomers or diastereomers?

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