Question

13.) Provide a synthesis for the target molecule shown. (18 pts)product. (6 pts)

Bonus: (10 pts)

Starting from Benzene and using reagents that we have discussed in class, design a synthesis for the Target molecule (TM)

13. Provide a synthesis for the target molecule shown. (18 pts) go alcohol aketone OH СОН M 얘 SM omgBr =sin 1-2 OH => KongBros Naz6.2010 H2SO4, H2O & H300 q Etmaira H20 어 #C=, 2° alcohol, aldehyde 20 TM o o #C77, Ketore talkere SM "OH O PCC I

Answer 1

OH PCC EtMgBr DCM H20+ OH O-THP NaBH MeOH DHPO-THP H, THE 1 03, Zn/H2O H2O

=H - Disamylborane, H2Oz/NaOH PPh-CH2-CHE CH 3-methylbut-1-yne 3-methylbutanal (Z)-5-methylhex-2-ene 3-methylbut-1-yne react with disamylborane and H2Oz/NaOH to form 3-methylbutanal 3-methylbutana react with wittig reagent to form (Z)-5-methylhex-2-ene ooh HNO3 M NO2 Na,s NH2 NaNO2.HCI HBF4 . Il H2SO4 Dinitration NO2 NO2 partial nitro reduction NaNO2.HCI CuCN F Formaldehyde, formic acid Hz. Pd/C MeOH, NaBH4 NH2