[Big-Daddy]

Are there any molecules for which it is not possible to indicate the 3D shape of the molecule and its structure using the wedge/dashed bonds notation for the stereochemistry? For example (sorry but I have no idea of the IUPAC name) the product of the Diels-Alder reaction between cyclohexadiene and acrolein (see "asymmetric DA reactions" here: http://en.wikipedia.org/wiki/Diels%E2%80%93Alder_reaction) - this structure is quite blatantly three dimensional. Is that because it isn't possible to draw it in 2 dimensions using the normal stereochemistry notation?

[discodermolide]

In 2 dimensions it looks like this note the smiles engine put the word chiral in there.

[Big-Daddy]

Oh so it can be drawn in 2D ... do you know of any molecules that cannot? i.e. that cannot be drawn in 2D in theory, even though sometimes it might be impractical.

BTW there are 3 chiral centres which makes the stereochemistry important, does this mean that your currently dashed bond to C=O might become wedged in a stereisomer?

[discodermolide]

Well yes it would be a wedge in a stereoisomer.
I drew the molecule as it was described on the Wiki page with the aldehyde "down"
Here the aldehyde is "up"



To answer your other question, I don't know!

[Big-Daddy]

Well yes it would be a wedge in a stereoisomer.
I drew the molecule as it was described on the Wiki page with the aldehyde "down"
Here the aldehyde is "up"



To answer your other question, I don't know!

OK, thanks for your *delete me*