cheminform abstract: stereoselective synthesis of (3r,3as,7as*)-3-aryloctahydroindol-2-ones using...

1999 stereochemistry stereochemistry (general, optical resolution) O 0030 45 - 047 Stereoselective Synthesis of (3R*,3aS*,7aS*)-3-aryloctahydroindol- 2-ones Using Radical Cyclization: A Formal Synthesis of (±)- Pancracine. — N-(cyclohex-2-enyl)acetamides (I) or (III) undergo 5-exo-trig radical cyclization in the presence of (Tms) 3 SiH (or Bu 3 SnH) and catalytic amounts AIBN to give cis fused products as single diastereomers. Product (IV) is converted to polycycle (V), which was already applied as key intermediate in the synthesis of alkaloid pancracine (VI). In contrast, N- (cyclohex-1-enyl) derivatives like amide (VII) react with (Tms) 3 SiH or Bu 3 SnH in a 5-endo-trig manner to give mixtures of cis- and trans-fused products (ca.1:1 to ca.1:2). — (IKEDA, MASAZUMI; HAMADA, MASAHIRO; YAMASHITA, TAKASHI; MATSUI, KATSUAKI; SATO, TATSUNORI; ISHIBASHI, HI- ROYUKI; J. Chem. Soc., Perkin Trans. 1 (1999) 14, 1949-1956; Kyoto Pharm. Univ., Misasagi, Yamashina, Kyoto 607, Japan; EN) 1

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Page 1: ChemInform Abstract: Stereoselective Synthesis of (3R*,3aS*,7aS*)-3-aryloctahydroindol-2-ones Using Radical Cyclization: A Formal Synthesis of (.+-.)-Pancracine

1999 stereochemistry

stereochemistry (general, optical resolution)O 0030

45 - 047Stereoselective Synthesis of (3R*,3aS*,7aS*)-3-aryloctahydroindol-2-ones Using Radical Cyclization: A Formal Synthesis of (±)-Pancracine. — N-(cyclohex-2-enyl)acetamides (I) or (III) undergo5-exo-trig radical cyclization in the presence of (Tms)3SiH (or Bu3SnH) andcatalytic amounts AIBN to give cis fused products as single diastereomers.Product (IV) is converted to polycycle (V), which was already applied askey intermediate in the synthesis of alkaloid pancracine (VI). In contrast, N-(cyclohex-1-enyl) derivatives like amide (VII) react with (Tms)3SiH or Bu3SnHin a 5-endo-trig manner to give mixtures of cis- and trans-fused products (ca.1:1to ca.1:2). — (IKEDA, MASAZUMI; HAMADA, MASAHIRO; YAMASHITA,TAKASHI; MATSUI, KATSUAKI; SATO, TATSUNORI; ISHIBASHI, HI-ROYUKI; J. Chem. Soc., Perkin Trans. 1 (1999) 14, 1949-1956; Kyoto Pharm.Univ., Misasagi, Yamashina, Kyoto 607, Japan; EN)

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