Synthesis Golf I: Sodium Fluvastatin
Edit: step count is 15, longest linear sequence of 9 steps

Just to (hopefully) get the ball rolling, here's something I scribbled down. I am sure people here will have better answers. And I have not done a lot of literature research to see whether the steps are plausible, so there might be fatal flaws... but hopefully not; as far as I know/can tell, everything here is relatively sensible.

Retrosynthesis first. I chose a Horner–Wadsworth–Emmons reaction to make the (E)-double bond, and something similar to the Reissert synthesis for the indole. It's not exactly the same because I didn't acylate the benzylic carbon, but the initial disconnection is similar. This leads to the key building blocks:



I chose the C(sp2)-C(sp3) bonds in 2 to disconnect. One can be made by SNAr with the amazing SNAr substrate 1-fluoro-2-nitrobenzene (5), and the other by Pd cross-coupling (I'm guessing cheaper ways probably exist). I've never actually seen SNAr reactions with enolates as nucleophiles, but I guess that if it doesn't work, SRN1-type conditions should still make that step possible:



As for 3, I figured it could be made from a symmetrical intermediate:





Forward synthesis

Synthesis of 3, starting from cyclopentadiene:




  (i) $\ce{BH3.THF}$, then $\ce{H2O2, NaOH}$; (ii) TBSCl, imidazole; (iii) $\ce{O3}$, then $\ce{H2O2}$; (iv) $\ce{TMSCHN2}$; (v) enzymatic desymmetrisation (I did not look up specifically which, but I think it should be possible); (vi) 7, NaH


Next, the synthesis of 2, starting from methylglyoxal:




  (vii) ethylene glycol, TsOH; (viii) Pd cat., ligand, $\ce{NaO^{t}Bu}$, 6; (ix) NaH, 5


Forming the indole:




  (x) Zn, AcOH; (xi) $\ce{NaH, ^{i}PrI}$; (xii) aq. HCl


and finally the HWE, the TBS deprotection, and the last redox step, a diastereoselective boron reduction. I wasn't entirely sure if it would work on an α,β-unsaturated ketone, but Comp Org Synth II, section 8.01 has several examples of it being used on an α,β-unsaturated ketones.




  (xiii) LiHMDS, 3; (xiv) $\ce{TBAF, H2O}$; (xv) $\ce{Et2B(OMe), NaBH4}$