Table 7.

Reported total syntheses of the Amaryllidaceae isocarbostyrils

isocarbostyril	research group	publication year	number of stepsa	overall yielda	reference
(+)-narciclasine	Rigby	1997	23	0.2%	183, 184
(+)-narciclasine	Hudlicky	1999	9	0.6%	185, 146
(+)-narciclasine	Keck	1999	14	16%	162
(+)-narciclasine	Yan	2002	13	17%	186
(±)-pancratistatin	Danishefsky	1989	27	0.16%	187
(+)-pancratistatin	Hudlicky	1995	14	2%	188, 189
(+)-pancratistatin	Trost	1995	19	8%	190
(+)-pancratistatin	Haseltine	1997	24	0.97%	191
(+)-pancratistatin	Magnus	1998	22	1.2%	192, 193
(+)-pancratistatin	Rigby	2000	23	0.35%	184
(+)-pancratistatin	Pettit	2001	10	3.6%	109b
(±)-pancratistatin	Kim	2002	21	4%	194, 195
(+)-pancratistatin	Li	2006	13	9%	196
(±)-7-deoxynarciclasine	Ohta, Kimoto	1975	20	1.5%	197, 198, 199
(+)-7-deoxynarciclasine	Paulsen	1982	12	4%	200, 201
(±)-7-deoxynarciclasine	Schubert	1987	18	7.2%	202c
(+)-7-deoxynarciclasine	Ogawa	1991	23	0.04%	203, 204
(+)-7-deoxynarciclasine	Hudlicky	1992	8	12%	205, 206
(±)-7-deoxynarciclasine	Martin	1993	11	4%	207
ent-7-deoxynarciclasine	Keck	1996	14	11%	161, 162
(+)-7-deoxynarciclasine	Keck	1999	11	27%	162
(+)-7-deoxynarciclasine	Yan	2002	15	11%	208
(±)-7-deoxynarciclasine	Padwa	2006	15	10%	209, 210
(+)-7-deoxypancratistatin	Paulsen	1982	9	6.5%	200, 201
(+)-7-deoxypancratistatin	Keck	1995	22	4%	211, 212
(+)-7-deoxypancratistatin	Hudlicky	1995	12	2.6%	213
(+)-7-deoxypancratistatin	Hudlicky	1995	10	3%	213, 189
(+)-7-deoxypancratistatin	Chida	1996	29	0.03%	214
(+)-7-deoxypancratistatin	Keck	1998	15	12%	215
ent-(−)-7-deoxypancratistatin	Hudlicky	1999	14	1%	163
(+)-7-deoxypancratistatin	Plumet	2000	21	3%	216
(+)-7-deoxypancratistatin	Madsen	2006	13	1.4%	217
(+)-7-deoxypancratistatin	Madsen	2006	15	4.3%	217
(±)-7-deoxypancratistatin	Padwa	2006	23	3%	218, 210
(±)-trans-dihydronarciclasine	Cho	2007	15	11%	219
(±)-7-deoxy-trans-dihydronarciclasine	Tsuda	1978	16	1.1%	220
(+)-7-deoxy-trans-dihydronarciclasine	Chida	1996	24	0.18%	214
(+)-7-deoxy-trans-dihydronarciclasine	Iwabuchi	2005	24	1.4%	221

^aNumber of steps and overall yield from commercially available starting material for the longest linear sequence. One-pot procedures are counted as one step. If the utilized starting material is not commercially available, but had been reported previously by other investigators, the number of steps and yields were taken from the cited sources.

^bRelay synthesis from (+)-narciclasine.

^cImprovement of the synthesis by Ohta and Kimoto (Ref. ²⁰¹).