1,1-Bis(4-hydroxyphenyl)-2-phenylbut-1-ene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following same procedure of Mitsunobu reaction as described in example 16, step D, 4,4′-(2-phenylbut-1-ene-1,1-diyl)diphenol (220 mg, 0.473 mmol) was reacted with (1-methylpyrrolidin-2-yl)methanol (82 mg, 0.712 mmol, made from DL-proline Following Arch. Pharm. Phamz. Med. Chem. 1996, 329, 95-104.) to give 65 mg desired product (33% yield). m/z=414[M+1]+. procedure of Mitsunobu reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following same procedure of Mitsunobu reaction as described in example 16, step D, 4,4′-(2-phenylbut-1-ene-1,1-diyl)diphenol (220 mg, 0.473 mmol) was reacted with (1-methylpyrrolidin-2-yl)methanol (82 mg, 0.712 mmol, made from DL-proline Following Arch. Pharm. Phamz. Med. Chem. 1996, 329, 95-104.) to give 65 mg desired product (33% yield). m/z=414[M+1]+. procedure of Mitsunobu reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the same procedure as described in example 16, step D & E, 4-(1-(4-hydroxylphenyl)-2-phenylbut-1-enyl)phenol (150 mg, 0.474 mmol) was reacted with (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (107 mg, 0.571 mmol), followed by de-Boc in condition of TFA/CH2Cl2, to give the desired product (36 mg, 20% yield, Z/E=1/1). m/z=386[M+1]+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the same procedure as described in example 16, step D & E, 4-(1-(4-hydroxylphenyl)-2-phenylbut-1-enyl)phenol (150 mg, 0.474 mmol) was reacted with (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (107 mg, 0.571 mmol), followed by de-Boc in condition of TFA/CH2Cl2, to give the desired product (36 mg, 20% yield, Z/E=1/1). m/z=386[M+1]+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 4-(1-(4-hydroxylphenyl)-2-phenylbut-1-enyl)phenol (500 mg, 1.0 eq), (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (480 mg, 1.5 eq) and PPh3 (625 mg, 1.5 eq) in 25 mL anhydrous THF under nitrogen was added DIAD (480 mg, 1.5 eq) dropwise at 0° C. The reaction was stirred for 48 h at rt. Then the reaction was quenched with water and extracted with EtOAc. The extract was dried, concentrated and purified by column chromatography to give the desired product (400 mg, 51% yield, Z/E=1/1). Then the reaction was quenched with water extracted with EtOAc The extract was dried concentrated purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following general procedure of McMurry reaction as described in example 1, step B, propiophenone (1.9 g, 3.0 eq) was reacted with bis(4-hydroxyphenyl)-methanone (1.0 g, 1.0 eq) to give 1.3 g desired product (88% yield). general procedure of McMurry reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following same procedure of Mitsunobu reaction as described in example 16, step D, 4,4′-(2-phenylbut-1-ene-1,1-diyl)diphenol (220 mg, 0.473 mmol) was reacted with (1-methylpyrrolidin-2-yl)methanol (82 mg, 0.712 mmol, made from DL-proline Following Arch. Pharm. Phamz. Med. Chem. 1996, 329, 95-104.) to give 65 mg desired product (33% yield). m/z=414[M+1]+. procedure of Mitsunobu reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the same procedure as described in example 16, step D & E, 4-(1-(4-hydroxylphenyl)-2-phenylbut-1-enyl)phenol (150 mg, 0.474 mmol) was reacted with (S)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (107 mg, 0.571 mmol), followed by de-Boc in condition of TFA/CH2Cl2, to give the desired product (36 mg, 20% yield, Z/E=1/1). m/z=386[M+1]+.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 4-(1-(4-hydroxylphenyl)-2-phenylbut-1-enyl)phenol (500 mg, 1.0 eq), (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (480 mg, 1.5 eq) and PPh3 (625 mg, 1.5 eq) in 25 mL anhydrous THF under nitrogen was added DIAD (480 mg, 1.5 eq) dropwise at 0° C. The reaction was stirred for 48 h at rt. Then the reaction was quenched with water and extracted with EtOAc. The extract was dried, concentrated and purified by column chromatography to give the desired product (400 mg, 51% yield, Z/E=1/1). Then the reaction was quenched with water extracted with EtOAc The extract was dried concentrated purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following general procedure of McMurry reaction as described in example 1, step B, propiophenone (1.9 g, 3.0 eq) was reacted with bis(4-hydroxyphenyl)-methanone (1.0 g, 1.0 eq) to give 1.3 g desired product (88% yield). general procedure of McMurry reaction