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. 2020 Jan 19;25(2):414. doi: 10.3390/molecules25020414

Table 1.

Pictet-Spengler reaction in total synthesis of natural products.

Target Scheme/Figure P-S Carbonyl Partner and Catalyst Note [Ref]
(±)-cribrostatin 4
(±)-renieramycin G		 Scheme 20
Figure 3 		(EtO)2CHCH2OBz
TMSOTf 		cytotoxic studies [82,83,84,85]
(±)-hamayne Figure 3 CH2O/HCO2H crinine type alkaloids [86]
(±)-lycorane Figure 3 CH2O/HCl Amaryllidaceae family [87]
(−)-saframycin A Scheme 21 OHC-CH2NHCbz
CF3CH2OH, AcOH, 4 Å MS 		intermolecular P-S (C-1)
intramolecular
P-S (C-11)		 [88]
mitragynine, paynantheine, speciogynine Scheme 22 Aldehyde 80
Thiourea-derived catalysts 		Mitragyna yohimbinoid alkaloids [89]
(±)-tangutorine Scheme 23 Aldehyde 83
micRowave 		the same cytotoxic activity for racemate and pure enantiomers [90]
(−)-lemonomycin Figure 3 Cinnamaldehyde
CSA, TMSCN 		potent activity against drug-resistant cocci [91]
tetracyclic core of lemonomycin Figure 3 OHC-CO2Et
CF3CH2OH, AcOH,
4 Å MS 		substrate-induced stereocontrol strategy [92]
venenatine
alstovenine 		Scheme 24 Compound 86
HCl (aq) oR DMAP oR NaI 		yohimbinoid alkaloids
C-3 stereochemistry		 [93]
3-arylacrilamide (C-1)-side chain derivatives Figure 3 OHC-CH2NHCbz
NaOAc/AcOH 		saframycin/ecteinascidin type compounds [94,95]
(+)-lochnerine
(+)-dispegatrine 		Figure 3 OHC(CH2)2CO2Me
AcOH 		sarpagine type [96]
(−)-jorunnamycins A, C
(−)-jorumycin		 Scheme 26 Compound 89
CF3CH2OH, AcOH 		renieramycin type [97]
(−)-renieramycin G Scheme 26 Compound 89
CF3CH2OH, AcOH 		renieramycin type [98]
(±)-alstonerine Scheme 25 Compound 91
Wet CH2Cl2 		macroline/sarpagine type [99]
erysotramidine Scheme 25 Compound 93
H3PO4 		erythrina alkaloids [100,101]
(±)-actinophyllic acid Scheme 27 Different form of P-S indolohydroazocine [102]
cribrostatin 4
renieramycin I		 Scheme 28 (EtO)2CHCH2OBz TMSOTf/Ac2O synthesis of left-half renieramycin model compound [103,104]
(+)-yohimbine Figure 3 Reported in [65] - [105]
(−)-corynantheidine Figure 3 Reported in [65] corynanthe alkaloids [106]
(−)-corynantheine
(−)-dihydrocorynantheine		 Figure 3 Reported in [65] corynanthe alkaloids [107]
(−)-affinisine oxindole Figure 3 Reported in [66] - [108]