Table 3. Biomimetic Dimerization of Resveratrol.

entry	reaction conditions	10	16	53/55	18	57	ref
1	K3Fe(CN)6, K2CO3, MeOH/H2O, rt	23%	—	—	16%	—	(108)
2	horseradish peroxidase, aq acetone	13%	—	—	10%	—	(108)
3	soybean peroxidase, aq EtOH	12%	—	14%b	10%	—	(108)
4a	FeCl3·6H2O, CH2Cl2	—	7%	—	10%	—	(168)
5a	FeCl3·6H2O, CH2Cl2/MeOH (7:3 v/v)	—	—	—	—	29%	(168)
6a	Pt anode/cathode in MeCN/0.2 M LiClO4 (+1.00 V vs Ag/AgNO3)	—	8%	—	14%	—	(170)
7	horseradish peroxidase, acetone/pH 8.0 buffer	93%c	—	—	—	—	(148)
		(89%)d
8	horseradish peroxidase, acetone/pH 6.0 buffer	—	—	55%c,e	—	—	(148)
				(24%)d,e
9	horseradish peroxidase, acetone/pH 5.0 buffer	—	—	—	20%c	—	(148)
					(19%)d
10	horseradish peroxidase, acetone/pH 4.0 buffer	28%c	—	—	—	—	(148)
		(26%)d,f
11	NaNO2/pH 3.0 buffer, MeOH	2%	—	—	—	1%	(171)

^aR = Me (pterostilbene, 3).

^b2:1 mixture of 55/53.

^cHPLC yield.

^dIsolated yield.

^eProduct was 53.

^fcis-δ-viniferin is major pdt.