Synthesis Golf IX: Tezacaftor A full FAQ post has been written on meta.chem.SE, explaining the premise of synthesis golf and the 'rules'. Please take a look at this before answering (if you haven't already).



The target of this Easter special round of synthesis golf is tezacaptor, which has recently been approved by the FDA as a treatment for cystic fibrosis in combination with ivacaftor: 



InChI=1S/C26H28F2N2O6/c1-24(2,14-32)22-10-15-9-17(4-5-19(15)30(22)12-18(33)13-31)29-23(34)25(7-8-25)16-3-6-20-21(11-16)36-26(27,28)35-20/h3-6,9-11,18,31-33H,7-8,12-14H2,1-2H3,(H,29,34)/t18-/m1/s1


Any commercial starting material is acceptable (as previously, commercial meaning you can buy it from Sigma-Aldrich) providing it has 10 or fewer carbons 
The synthesis must include a cyclopropanation (i.e. the starting materials cannot contain a cyclopropane)
The synthesis should ideally provide a single stereoisomer of the hydroxyl stereo centre, but to keep things more accessible, a racemic synthesis won't be criticised
I am really glad that you are reviving these challenge questions NotEvans.
As for the synthesis, the amide disconnection leading to fragments A and B seems like the most simplifying first disconnection:

Synthesis of fragments A and B is outlined below:



Esterification of the readily available acid with isopropyl alcohol under Yamaguchi conditions;
Demethylation (this is why I've chosen to make the isopropyl ester, it shouldn't be destroyed with $\ce{BBr3}$);
Formation of a thiocarbonate crucial for the introduction of two fluorine atoms;
JACS 2010, 132(51), 18199;
Aldol condensation of the ester with formaldehyde;
Ester hydrolysis;
Conversion of the acid to acyl chloride.





p-Nitroaniline is brominated;
Sonogashira coupling;
Gold-catalyzed hydroamination;
Fmoc protection of the indole nitrogen turned out to be necessary at this point (so it doesn't interfere with the coupling with fragment A);
Reduction of the nitro group.


Now comes the endgame:




Amide formation;
Corey-Chaykovsky reaction of a stabilized sulfure ylide is selective for enone-like systems;
Piperidine removes Fmoc;
The indole nitrogen attacks glycidol thus opening the epoxide on the more accessible site;
Reduction of the ester with $\ce{LiBH4}$ should be selective. Several equivalents are needed because of the free hydroxyl groups. My only concern is the stability of the cyclopropane, but other hydride donors could be tried.


EDIT: Here is the synthesis of the alkynyl ester needed to make fragment B:

18. Methylacetoacetate is methylated twice;


Formation of enol triflate;
Base-induced elimination of the triflate gives the ester.



  Total step count: 20
  
  Longest linear sequence: 12