5(1H)-Indolizinone,2,3,8,8a-tetrahydro-,(8aS)-(9CI) synthesis

Yield:-

Steps:

Multi-step reaction with 5 steps
1.1: 89 percent / iodine; imidazole; triphenylphosphine / diethyl ether / 12 h / 20 °C
2.1: CuI / tetrahydrofuran / 0.5 h / -40 - -10 °C
2.2: 87 percent / tetrahydrofuran / 3 h / -40 - 20 °C
3.1: 99 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C
4.1: 65 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C
5.1: 74 percent / (1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)Cl₂(PCy₃)RuCHPh / CH₂Cl₂ / 3 h / 20 °C

References:

Park, So Hyun;Kang, Hyun Jung;Ko, Sangwon;Park, Soyoung;Chang, Sukbok [Tetrahedron Asymmetry,2001,vol. 12,# 18,p. 2621 - 2624]