What Makes a Synthesis Elegant?

This is a topic that I've been wondering about for some time.  I'll often hear someone (or an abstract if they're not-so-humble) describe a synthesis as being elegant.  It's definitely not a word that's thrown around the scientific community often, as we tend to be more concerned with results, data, and other unemotional things.  However there tends to be a push towards finding 'elegant' solutions to syntheses, and more often than not an elegant solution will be prized above one that was published earlier.

So what, exactly, makes a synthesis elegant?  Asking around today brought me a variety of answers.  Most came in two parts.  First they highlighted certain types of reactions and solutions, citing stereoselectivity, strategic bonding, and the like.  Then, most said something along the lines of, "an elegant synthesis should make you feel like you are looking at a piece of art."  Given that last sentence and that all 'elegant' solutions are different, quantifying this would be impossible.  But there's no harm in trying!

After talking it over, looking up syntheses, and musing to myself, here's how you go about making an elegant synthesis:

1. It must be short.  Like 10-20 steps total short.
2. It must rapidly generate complexity.  Taking 5 steps to protect/deprotect isn't helping you.
3. It must have some novel or unique approach.  Not necessarily complex reactions, just combining more basic ones in a way no one has thought of before is fine.
4. If it's a newly synthesized compound, you get bonus points.

At the end of the day, there are going to be some reactions that fit these rules that won't be considered elegant.  And elegant solutions are not always going to follow this approach.  When it comes down to it, when you see an elegant synthesis, you will be able to appreciate it.  And I suppose that comes with experience.  I imagine its like watching a Grand-master play chess.  To the uninitiated, it may be a convoluted mess with no real pattern until suddenly, check-mate.  To an experienced player, however, each move carries significance, strategy, and meaning.  So that as you watch, it transcends being a game, and becomes a work of art.  

-Woodward

Some thoughts from twitter 

@NatureChemistry @WoodwardRB - But seriously: "Elegance" utilizes strategic bonds and interesting reactions synergistically (1/2)
— See Arr Oh (@SeeArrOh) August 14, 2013

@NatureChemistry @WoodwardRB - "Elegance" causes a deep, fundamental emotional reaction to the work as a whole, like a contented sigh (2/2)
— See Arr Oh (@SeeArrOh) August 14, 2013

@WoodwardRB A synthesis that makes me feel the design of the route did all the work. (1/2)
— Stephen Davey (@stephengdavey) August 14, 2013

@WoodwardRB So that at each step it seems like the molecule is just being encouraged rather than forced to do something.(2/2)
— Stephen Davey (@stephengdavey) August 14, 2013

@WoodwardRB Early generation of one asymmetric center, and then diastereoselective rxns to generate all others, Ex: http://t.co/gNQs72uy9R
— Thomas GD (@ThomasGaleandro) August 14, 2013

@WoodwardRB More generally : its shortness, with rapid generation of complexity. Bonus if it uses wisely catalysts ;)
— Thomas GD (@ThomasGaleandro) August 14, 2013

@WoodwardRB I would say synthesis is elegant if there is a beautiful usage of rearrangement that cuts the sequence down for several steps
— Xydja (@Xydja) August 14, 2013

Leave feedback on what you think makes a synthesis 'elegant' or leave an example of an example of an elegant synthesis.