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Where can I learn more about organic synthesis?

Books specifically about synthesis planning:

Other useful books:

  • Classics in Total Synthesis I 1996, II 2003 and III 2011, K. C. Nicolaou et. al..
    Very readable books covering a variety of total syntheses. Each chapter introduces the large, describes the retrosynthesis, and then covers the forward synthesis in detail, explaining any issues of selectivity or problems encountered.

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What should my answer include/ are there any rules?

Answers should at least include:

  • A forward synthesis, giving the structures of key intermediates, and the reagents used. Its not expected that there'll be beautiful figures with full reagents/ equivalents/ temperatures/ times/ yields, but there needs to be enough for the reader to tell whats going on.
  • References for critical/ unusual steps. (There is no need to reference a Swern oxidation, but a 10 component domino reaction needs some precedence.)
  • A brief commentary as to your synthetic strategy/ approach.
  • A step count, giving the total number of steps, and the steps in your longest linear sequence (if the route is convergent). This will be verified and posts edited to give the true step count.

Ideally, in order to help others learn from your approach, answers would also include:

  • A retrosynthesis, showing the key disconnections you plan to make, and where this takes you back to.
  • Explanations for key stereo controlling steps, e.g. a transition state for an aldol.

In order to keep things fair, some ground rules have been established.

  • Your synthesis must start from materials available from Sigma Millipore (formerly Sigma Aldrich; an arbitrary choice, but most people have access to either the website or a physical catalogue). This means no starting from random intermediates that you hypothesise.
  • Your synthesis cannot be a verbatim re-hash of a published procedure, i.e. no copying a direct route towards the target. Inspiration is fine, i.e. you can use a Horner–Wadsworth–Emmons reaction (HWE) even if the published route also uses a HWE.
  • Your synthesis must include a way of introducing whatever functionality is specified in the challenge itself, for example in the Fluvastatin challenge, the heterocycle had to be made, rather than buying pyrrole and functionalising.

As an example of a good answer to synthesis golf, this post by orthocresol might be useful.

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What is synthesis-golf?

Chemistry.SE has the same problems as many other communities on the Stack Exchange network, namely that the bulk of questions are at a basic level. The effect of this is that the majority of questions quickly receive answers, which rely on basic fundamental knowledge or a quick google search, without many people getting the chance to participate. Compared to the language communities where people post looking for translations/grammar explanations, and many people are able offer their thoughts and a range of different answers are provided, fewer users can be engaged here.

Synthesis golf aims to encourage participation on chem.SE by providing synthetic challenges at an appropriate level that they should appeal to students and practicing chemists alike. Additional bounties are applied to further persuade people to take part.

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    $\begingroup$ This is a good description of why we have added synthesis-golf but not about what is synthesis-golf. I'd love to edit this post, but I am not quite sure of what synthesis golf is exactly, so I'll leave it for someone else to edit it. $\endgroup$
    – Pritt says Reinstate Monica
    Commented Jun 29, 2017 at 1:39
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Can I post my own synthesis golf challenges on chemistry.SE?

In order to avoid there being 'too much of a good thing'/ 'spamming the homepage', it's been agreed that it would be sensible to post these challenges at regular, monthly intervals.

If you have an idea for a target or challenge, first check that it falls within the scope of synthesis golf as defined here, then suggest it in chat. If it seems like it would make a good synthesis golf challenge, then we'll use it for a future challenge.

Additionally there is a related meta thread searching for new targets: Suggestions for synthesis-golf targets.

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I can't quite get to a full answer, can I participate anyway?

The point of synthesis golf is to get as many people involved as possible, so yes. If you have a proposed synthesis with a few gaps then feel free to post it anyway. It's quite likely that someone will be able to help you out and point you in the right direction to finish!

What should be avoided is the posting of heavily incomplete answers with the intention of editing them at some point in the future. Stack Exchange is clever enough to 'save' your draft answer so you can come back to it, avoiding the need to post and edit constantly as you work out more of the synthesis.

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This is all very organic, will there be any other kinds of golf on Chemistry.se?

Synthesis golf itself could already be expanded to other areas of synthesis (inorganic synthesis, materials synthesis etc), and indeed this may be looked at in future challenges.

For the time being, and taking into account the people active on here, organic synthesis is the area most likely to gain a range of answers, not to mention that there are a lot more possibilities for synthesising an organic molecule than for an inorganic complex.

Other kinds of golf (computational golf, theoretical golf) could also work, but fall beyond the scope of . If you're interested in this, perhaps bring it up on chat, or make a post in meta to gain some feedback.

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Aren't synthesis golf questions too broad, and therefore off-topic?

Necessarily, synthesis golf challenges will be somewhat 'broad', as there are many possible answers rather than a single one. That is, however, the entire point of synthesis golf - it requires more than one person to give a definition/ copy some values.

Based on this, hopefully, no, the questions aren't too broad. At the time of writing this, only one challenge has been posted, which was well received generally, though some concerns were raised about how 'broad' the question was.

Future challenges will narrow the scope of what is being asked, focusing on small parts of molecules with interesting moieties, rather than asking for synthetic routes to entire molecules. This should address fears about the overly broad nature of synthesis golf.*

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* I would add that is an attempt to do something different to engage people on Chemistry.SE and generally raise the bar of the level of questions being asked. Even if the challenges are pushing the limits of whats allowed here (and I do think they are within the limits of whats allowed), there is an argument to say that if they're succeeding in getting people involved, and if they are having the desired effect, then the boundaries can be pushed. Basically, please don't flag as off-topic, if you have specific issues we can talk about them in chat or here on meta.

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What is the correct answer?

Necessarily there is no one correct answer, which is why this works, many people can provide what they subjectively think is a good answer based upon the chemistry they know.

At the end of the month for which a given challenge is 'active', the answer will be awarded to whichever solution provides a convincing solution in the shortest number of steps in the longest linear sequence, which might also be the total step count depending on how the route is proposed.*

As stated here, bounties will also be awarded for things other than step count, such as creativity, use of unusual reactions etc.

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* Step count isn't the most important thing in a synthesis, other factors like yield and efficiency must also be taken into account, however, whether you like it or not, step count is and continues to be a well used metric for comparing organic syntheses, especially in the field of total synthesis.

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    $\begingroup$ Is it worth exploring scale up or commercial feasibility? e.g. anyone validly suggesting NaOCl or hydrogen peroxide over Dess-Martin periodinane is a step ahead for commercial feasibility $\endgroup$
    – Beerhunter
    Commented Jun 12, 2017 at 22:06
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How often does synthesis golf take place/how long does the challenge run for?

The current idea is to introduce a new synthesis golf challenge once a month, posted by NotEvans or orthocresol.

There is no specific 'end date' for a particular challenge. Feel free to go back and provide solutions to all of the previous ones. Nominally they'll be active for a period of a month, i.e. until the next one starts. During this period, bounties will be applied to encourage active participation.

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Should I retag old synthesis questions with ?

No. Questions relating about planning syntheses, synthetic strategy, published syntheses etc should continue to be tagged with and , along with other relevant tags such as or .

The tag is reserved specifically for questions arising from the synthesis golf challenge, it will be removed from all other questions if applied.

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What incentives are there for me to participate?

The aim of synthesis golf isn't to try and increase our users reputation. There will be at least one bounty during the one month period for which the challenge is 'active'. This will be derived from the reputation gained from asking the question. Other users may also choose to award bounties as they see fit.

Ultimately, the biggest incentive we can offer is the satisfaction of thinking up a good synthesis.

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I know nothing about organic synthesis but want to get involved, what can I do?

Whilst the challenges are meant to be approachable to people at a variety of stages of their chemical education, some people focus their interests on other areas of chemistry and necessarily won't have an interest in providing an answer. It would be nice if the whole community here on Chemistry.SE could be involved, however, some other things which you could do if you're interested:

  • Help edit posts to ensure they're readable/ fit in with the accepted standards, i.e. tidying up links to papers, introducing MathJax and mhchem where appropriate.
  • Vote. Up-vote answers that you think provide good solutions to the challenge and down-vote poor/ badly thought through answers if necessary.
  • Award bounties to encourage more people to participate. Obviously you're free to award these for whatever you see fit, e.g. prettiest schemes, the use of a name reaction from your country of birth, etc..

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Can I post multiple answers?

Yes. If you have two fundamentally different approaches, there is no problem with posting multiple answers to the same problem (as is the case with any question on Stack Exchange).

If, however, your two answers are essentially the same, but with minor differences (Swern vs TPAP, methyl ester vs benzyl ether), then its probably best to just include this information in your initial answer as a side note.

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