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A synthetic approach to taxane diterpenes. A synthesis of the bicyclo[5.3.1]undecenone ring system

✍ Scribed by Yasuo Ohtsuka; Takeshi Oishi

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 253 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)83977-5

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✦ Synopsis

Bicyclo[5.3.l]undecenone 2 corresponding to A and B rings in taxane diterpenes was synthesized. The eight-membered ring was constructed by a baseinduced intramolecular cyclization of twelve-membered lactam sulfoxides 15. 204 lja,b ya,bl,b2 isomer NC-S J K *H,6 5 4 9 07 / 11' 1 3 10 -. 2 0 H R NHMe 2_,R= H (A) mCPBA/CH C12. P K2C03/MeOH (reflux), (B) NaTeH/EtOH. Jones' reagent (62 %, 3-5, 4 steps), (C ethylene glycol/TsOH/benzene, DDQ/benzene (80°C) (69.5 %. 2 steps), CH3N02/i_Pr2NH/DMSO (75°C. 97 % based on consumed material), (D) MeONa/TiC13/AcONH4/

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