Synthetic studies on optically active furofuran and diarylbutane lignans^*

* This review was written in response to the author’s receipt of the JSBBA Award for Young Scientists in 2017.

Figures & data

Figure 1. Furofuran and diarylbutane lignans synthesized by our group.

Scheme 1. Asymmetric dimerization of cinnamic acid derivatives.

Table 1. Electrochemical oxidation of cinnamic acid derivatives.

Substrate: Ar	Temp. (°C)	F/mol	Yield (%) of 10	e.e. (%) of 18
	r.t	1.4	38	70
	0	1.4	42	73
	−20	1.6	47	82
	-40	1.4	47	91
	0	0.7	16(26)	72
	−20	1.3	24(32)	83
	0	0.7	10(22)	85
	−20	1.3	8(9)	87
	0	0.7	8(9)	40
	−20	1.3	8(9)	39

(): based on recovery.

Scheme 2. Synthetic approaches to furofuran lignans.

Scheme 3. Synthetic approaches to diarylbutane lignans.