"""Original solution schematic; Python 3.14, numpy 2.3.5, matplotlib 3.10.7. Writes its own PNG basename to the current working directory. """ from pathlib import Path import sys for candidate in Path(__file__).resolve().parents: if (candidate / 'tools' / 'chemistry_diagram.py').exists(): sys.path.insert(0, str(candidate)) break import numpy as np import matplotlib.pyplot as plt from matplotlib.patches import FancyArrowPatch, Circle from tools.chemistry_diagram import atom, bond, ring, wedge, curly, flow, finish, save, BLUE, ORANGE, GREEN def txt(ax,x,y,s,size=11,color='0.15',ha='center'): ax.text(x,y,s,ha=ha,va='center',fontsize=size,color=color) def couple(ax,a,b,label,rad=.3,offset=(0,0)): ax.add_patch(FancyArrowPatch(a,b,connectionstyle=f'arc3,rad={rad}',arrowstyle='<->',mutation_scale=10,color=BLUE,lw=1.3)) m=(np.asarray(a)+np.asarray(b))/2+np.asarray(offset) txt(ax,*m,label,10,BLUE) def benzene(ax,c=(0,0),scale=1): t=np.deg2rad([30,90,150,210,270,330]);pts=np.column_stack([np.cos(t),np.sin(t)])*scale+np.asarray(c) ring(ax,pts,{0:2,2:2,4:2});return pts def carbonyl(ax,c,left,right,oxy='O',tetra=False,down=None): x,y=c;o=(x,y+1);bond(ax,c,o,1 if tetra else 2);atom(ax,o,oxy) for q,label in [(left[0],left[1]),(right[0],right[1])]:bond(ax,c,q);atom(ax,q,label) if down:bond(ax,c,down[0]);atom(ax,down[0],down[1]) return o def box(ax,x,y,s,w=2.6,h=.8,color=BLUE,size=11): from matplotlib.patches import FancyBboxPatch ax.add_patch(FancyBboxPatch((x-w/2,y-h/2),w,h,boxstyle='round,pad=0.08',fc='white',ec=color,lw=1.2)) if '$' not in s and len(s)>29: import textwrap s='\n'.join(textwrap.wrap(s,width=29)) elif '$' in s and len(s)>35: size=min(size,8.5) txt(ax,x,y,s,size,color) def route(rows,title,figsize=(12,6)): fig,ax=plt.subplots(figsize=figsize) for i,row in enumerate(rows): y=-i*1.7 for j,entry in enumerate(row): x=j*4 if j%2==0:box(ax,x,y,entry,w=3.35,h=1.05,size=11) else:flow(ax,(x-1.7,y),(x+1.7,y));txt(ax,x,y+.4,entry,10) finish(ax,(-2,18),(-len(rows)*1.7+.3,1.4),title) fig.tight_layout();return fig fig,axs=plt.subplots(1,2,figsize=(13,5.5)) ax=axs[0];t=np.arange(6)*np.pi/3+np.pi/6;p=np.column_stack([np.cos(t),np.sin(t)]) ring(ax,p);a=p[0];b=p[-1] wedge(ax,a,(2,1),True);atom(ax,(2,1),r'$CH_2CHO$') wedge(ax,b,(2,-1),True);atom(ax,(2,-1),r'$CH_2CHO$') wedge(ax,a,(.8,2),False);atom(ax,(.8,2),'H') wedge(ax,b,(.8,-2),False);atom(ax,(.8,-2),'Me') finish(ax,(-2,3.3),(-2.7,2.7),'Select cis dialdehyde: H and Me on the opposite face') ax=axs[1] for y,s in [(2,'Enone reductive α-alkylation'),(.8,'HWE → exocyclic enoate → hydrogenation'),(-.4,'Ester reduction → cis diol → cis dialdehyde'),(-1.6,'Two late Z-selective ethylidene Wittig reactions')]:box(ax,4,y,s,w=7.3,h=.65,size=10) for y in [1.6,.4,-.8]:flow(ax,(4,y),(4,y-.4)) finish(ax,(-.1,8),(-2.7,2.7),'Postpone both Z alkenes until all hydrogenation is complete') fig.tight_layout() save(fig,'paper-1-q11-second-route.png')