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ChemicalBook CAS DataBase List [1S-[1alpha,2alpha(Z),4alpha]]-2-methyl-5-(2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl)-2-penten-1-ol
77-42-9

[1S-[1alpha,2alpha(Z),4alpha]]-2-methyl-5-(2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl)-2-penten-1-ol synthesis

13synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 6 steps
1: 1.) LDA, 2.) DMPU, O2, P(OEt)3 / THF, -90 deg C
2: LiAlH4 / tetrahydrofuran / 2 h / Heating
3: NaIO4 / H2O; ethanol / 0.67 h / Ambient temperature
4: 1.) NaN(SiMe3)2, 2.) H2O, H(+) / 1.) xylol, reflux, 2.) RT, 4 h
5: 62 percent / KN(SiMe3)2, 18-crown-6 / tetrahydrofuran / 4 h / -90 - -60 °C
6: 1.) Zn, TiCl4, 2.) DIBAH / 1.) THF, RT, 12 h, 2.) CH2Cl2, from -78 deg C to 0 deg C, 12 h

References:

Krotz, Achim;Helmchen, Guenter [Tetrahedron Asymmetry,1990,vol. 1,# 8,p. 537 - 540]