Question

Challenge question: Synthesis of Serotonin

Propose a pathway for the synthesis of the neurotransmitter Serotonin starting from benzene. You may use any other reagents you seem fit, but you must show all the intermediates. No limits on the numbers of steps.

Answer 1

I guess if no one wants to try this by tmrw i'll close it :S

Answer 2

Let me give it a shot. Im a bit rusty :P

Answer 3

I skipped the detailed mechanism but I used bartoli indole mechanism

Answer 4

it's upside down

Answer 5

mirror!

Answer 6

haha it is mirrored. Good stuff, though. I like that route, it's sophisticated. By the way, you missed the -OH para to the nitrogen on the ring :P

Answer 7

werid! It didnt' show mirror'd when I took the pic. What -OH?

Answer 8

haha it must've been when you uploaded it or something. uhh the one attached to the benzene ring para to the N haha

Answer 9

Oh. Didn't see that. Hmm....i'm trying to think if I can add it from this point, but I can't think of a method to get it para.

Answer 10

Hint?

Answer 11

What i had in mind was to first make phenol, then 4-aminophenol. Then work around that to build the other ring. But let me see if i can find a way to add the phenol as the last step.

Answer 12

Ya, i was thinking of making phenol to make a diketo ring and then making the indol, i vaguely remember something like that, if you have any other methods. I learned a few a while ago.