Question

8. (10 pts) Suggest an efficient reaction sequence for the preparation of each of the following compound from the indicated starting materials and any other necessary reagents. from (use twice) OH

Answer 1

* W an kom ma fauteng #rom ause twice) y mepBA Nmes RU RM (حم) : ۱۰ 08 Cul Li ph 2. CICS OH

Mesides MeO- Olen months catalyst WP11 CH Alkonył reagent MO X = CI, B, or F Cys ACs Ru-1a Methyl okste Ru Ru-1b Fischer-typ catxe, low activity Ru-to Ru-1d Decomposition products with X = Cland Br n Bunci n-BuBr Гоме Cross-coupling catalyst Mes Times With Z-dichloroethene, 6.0 mol %, 50 "C, 3 h: >98% conv., yield ND, ZE = 60:40 With ZE dibromoethene. 6.0 mol %, 50 °C, 3 h: 16% corr., yield NO, ZE = 33:46 CHA HOR CH11 HOR Phs iPhy (S) coriolic acid methyl ester (anti-inflammatory) B(pin) Xlor H) Ru-2 With virryl fluoride, 5.0 mol %, 23 °C, 24 h: <5% conv., yield NA ZE - NA Olefin metathesis catalyst c Possible pathways for Z selective CM with alkeryl halides and high-oxidation-state complexes Alkenyh-Br reagent Y NA II OA Ref. 29 Tetrahydrosiphonodiol (anti-tumour, immunosuppressant) GW Mer DHE Olefin metathesis catalyst M = Mo or W vi OA Alkenyl-Freagent AC Me MOCA MeOCTA 3 From isopirnaric acid (potassium channel activator Vili v il BA-