Oxindoles: Formal Total Syntheses of Bis-Cyclotryptamine. Alkaloids, (±)-Chimonanthine and (±)-Folicanthine
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1 FeCl 3 -Catalyzed Allylation Reactions onto 3-Hydroxy 2- Oxindoles: Formal Total Syntheses of Bis-Cyclotryptamine Alkaloids, (±)-Chimonanthine and (±)-Folicanthine Lakshmana K. Kinthada, Sai Raghavendra Medisetty, Amarchand Parida, K. Naresh Babu, and Alakesh Bisai* Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhopal, Madhya Pradesh , INDIA. alakesh@iiserb.ac.in Table of Contents Spectral graphics HPLC Traces X-ray Structure of 9g S2 S90 S91 - S98 S99 S101 S1
2 H N O OH HO 33 Br 1 H NMR (400 MHz, DMSO-D6) of compound C NMR (100 MHz, DMSO-D6) of compound 33 S2
3 Scanned copyy of mass spectrum of 33 S3
4 1 H NMR (400 MHz, CDCl 3 ) of compound 6e 13 C NMR (100 MHz, CDCl 3 ) of compound 6e S4
5 Scanned copyy of mass spectrum of 6e S5
6 1 H NMR (400 MHz, CDCl 3 ) of compound 13b C NMR (100 MHz, CDCl 3 ) of compound 13b S6
7 f1 (ppm) H NMR (400 MHz, CDCl 3 ) of compound 13c f1 (ppm) C NMR (100 MHz, CDCl 3 ) of compound 13c S7
8 1 H NMR (400 MHz, CDCl 3 ) of compound 13d C NMR (100 MHz, CDCl 3 ) of compound 13d S8
9 1 H NMR (400 MHz, CDCl 3 ) of compound 13e C NMR (100 MHz, CDCl 3 ) of compound 13e S9
10 1 H NMR (400 MHz, CDCl 3 ) of compound 13f 13 C NMR (100 MHz, CDCl 3 ) of compound 13f S10
11 Me Me N O 13f OH NH HRMSS of compound 13f S11
12 f1 (ppm) H NMR (400 MHz, CDCl 3 ) of compound 15b C NMR (100 MHz, CDCl 3 ) of compound 15b S12
13 Bn N O OBn 15b NBn HRMSS of compound 15b S13
14 1 H NMR (400 MHz, CDCl 3 ) of compound 15c C NMR (100 MHz, CDCl 3 ) of compound 15c S14
15 N O O N 15c HRMSS of compound 15c S15
16 H NMR (400 MHz, CDCl 3 ) of compound 9b (prepared following condition A) f1 (ppm) C NMR (100 MHz, CDCl 3 ) of compound 9b (prepared following condition A) S16
17 H NMR (400 MHz, CDCl 3 ) of compound 9d (prepared following condition A) C NMR (100 MHz, CDCl 3 ) of compound 9d (prepared following condition A) S17
18 1 H NMR (400 MHz, CDCl 3 ) of compound 9e (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) of compound 9e (prepared following condition A) S18
19 1 H NMR (500 MHz, CDCl 3 ) of compound 9f (prepared following condition A) 13 C NMR (125 MHz, CDCl 3 ) of compound 9f (prepared following condition A) S19
20 Scanned copy of mass spectrum of 9f (prepared following condition A) S20
21 1 H NMR (400 MHz, CDCl 3 ) of compound 14a (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) of compound 14a (prepared following condition A) S21
22 H NMR (400 MHz, CDCl 3 ) of compound 14b (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) of compound 14b (prepared following condition A) S22
23 f1 (ppm) H NMR (400 MHz, CDCl 3 ) of compound 14c (prepared following condition A) f1 (ppm) C NMR (100 MHz, CDCl 3 ) of compound 14c (prepared following condition A) S23
24 N O OMe 14c HRMS spectra of compoundd 14c (prepared following condition A) S24
25 1 H NMR (400 MHz, CDCl 3 ) of compound 9a (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) of compound 9a (prepared following condition A) S25
26 1 H NMR (400 MHz, CDCl 3 ) of compound 14d (prepared following condition A) 13 C NMR(100 MHz, CDCl 3 ) of compound 14d (prepared following condition A) S26
27 f1 (ppm) 1 H NMR (400 MHz, CDCl 3 ) of compound 14e (prepared following condition A) C NMR (100 MHz, CDCl 3 ) of compound 14e (prepared following condition A) S27
28 1 H NMR (400 MHz, CDCl 3 ) of compound 14f (prepared following condition A) C NMR (100 MHz, CDCl 3 ) of compound 14f (prepared following condition A) S28
29 Scanned copy of mass spectrum of 14f (prepared following condition A) S29
30 f1 (ppm) 1 H NMR (400 MHz, CDCl 3 ) of compound 16a (prepared following condition A) f1 (ppm) 13 C NMR (100 MHz, CDCl 3 ) of compound 16a (prepared following condition A) S30
31 1 H NMR (400 MHz, CDCl 3 ) of compound 16b (prepared following condition A) f1 (ppm) 13 C NMR (100 MHz, CDCl 3 ) of compound 16b (prepared following condition A) S31
32 1 H NMR (400 MHz, CDCl 3 ) of compound 16c (prepared following condition A) C NMR (100 MHz, CDCl 3 ) of compound 16c (prepared following condition A) S32
33 1 H NMR (400 MHz, DMSO-D6) of compound 9f (prepared following condition A) f1 (ppm) C NMR (100 MHz, DMSO-D6) of compound 9f (prepared following condition A) S33
34 Scanned copy of mass spectrum of compound 9f (prepared following condition A) S34
35 1 H NMR (400 MHz, CDCl 3 ) of compound 21a 13 C NMR (100 MHz, CDCl 3 ) compound 21a S35
36 f1 (ppm) H NMR (400 MHz, CDCl 3 ) of compound 21b f1 (ppm) C NMR (100 MHz, CDCl 3 ) of compound 21b S36
37 CO 2 Me N O OH 21b OMe HRMSS of compound 21b S37
38 f1 (ppm) H NMR (400 MHz, CDCl 3 ) of compound 21c 13 C NMR (100 MHz, CDCl 3 ) of compound 21c S38
39 Me O S O N O OH 21c OMe HRMSS of compound 21c S39
40 H NMR (400 MHz, CDCl 3 ) of compound 22a (prepared following condition A) f1 (ppm) C NMR (100 MHz, CDCl 3 ) of compound 22a (prepared following condition A) S40
41 1 H NMR (400 MHz, CDCl 3 ) of compound 22b (prepared following condition A) C NMR (100 MHz, CDCl 3 ) of compound 22b (prepared following condition A) S41
42 f1 (ppm) H NMR (400 MHz, CDCl 3 ) of compound 22c (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) of compound 22c (prepared following condition A) S42
43 Scanned copy of mass spectrum of 22c (prepared following condition A) S43
44 1 H NMR (400 MHz, CDCl 3 ) of compound 25a 13 C NMR (100 MHz, CDCl 3 ) of compound 25a S44
45 Me N O Me Me O 25a O HRMSS of compound 25a S45
46 f1 (ppm) H NMR (400 MHz, CDCl 3 ) of compound 25b 13 C NMR (100 MHz, CDCl 3 ) of compound 25b S46
47 Me N O MeO Me Me O 25b O HRMSS of compound 25b S47
48 H NMR (400 MHz, CDCl 3 ) of compound 25c f1 (ppm) C NMR (100 MHz, CDCl 3 ) of compound 25c S48
49 Me N O Cl Me Me O 25c O HRMSS of compound 25c S49
50 Bn N O O O Me 25d Me 1 H NMR (400 MHz, CDCl 3 ) of compound 25d C NMR (100 MHz, CDCl 3 ) of compound 25d S50
51 Bn N O Me Me O 25d O HRMSS of compound 25d S51
52 f1 (ppm) H NMR (400 MHz, CDCl 3 ) of compound 25e f1 (ppm) C NMR (100 MHz, CDCl 3 ) of compound 25e S52
53 Me N O Me O 25e O HRMSS of compound 25e S53
54 1 H NMR (400 MHz, CDCl 3 ) of compound 25f 13 C NMR (100 MHz, CDCl 3 ) of compound 25f S54
55 Me N O Nphth Me O O 25f HRMSS of compound 25f S55
56 H NMR (400 MHz, CDCl 3 ) compound 2a (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) compound 2a (prepared following condition A) S56
57 1 H NMR (400 MHz, CDCl 3 ) compound 2b (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) compound 2b (prepared following condition A) S57
58 1 H NMR (400 MHz, CDCl 3 ) compound 2c (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) compound 2c (prepared following condition A) S58
59 Scanned copy of mass spectrum of 2c (prepared following condition A) S59
60 1 H NMR (400 MHz, CDCl 3 ) compound 2d (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) compound 2d (prepared following condition A) S60
61 H NMR (400 MHz, CDCl 3 ) compound 2e (prepared following condition A) f1 (ppm) 13 C NMR (100 MHz, CDCl 3 ) compound 2e (prepared following condition A) 0 S61
62 f1 (ppm) 1 H NMR (400 MHz, CDCl 3 ) compound 2f (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) compound 2f (prepared following condition A) S62
63 Scanned copy of mass spectrum of 2f (prepared following condition A) S63
64 H NMR (400 MHz, CDCl 3 ) of compound 2g (prepared following condition A) f1 (ppm) C NMR (100 MHz, CDCl 3 ) of compound 2g (prepared following condition A) S64
65 Scanned copy of mass spectrum of 2g (prepared following condition A) S65
66 H NMR (400 MHz, CDCl 3 ) of compound 2h (prepared following condition A) 13 C NMR (100 MHz, CDCl 3 ) of compound 2h (prepared following condition A) S66
67 1 H NMR (400 MHz, CDCl 3 ) of compound 2i (prepared following condition A) C NMR (100 MHz, CDCl 3 ) of compound 2i (prepared following condition A) S67
68 1 H NMR (400 MHz, CDCl 3 ) of compound 2j (prepared following condition A) C NMR (100 MHz, CDCl 3 ) of compound 2j (prepared following condition A) S68
69 Scanned copy of mass spectrum of 2j (prepared following condition A) S69
70 1 H NMR (400 MHz, CDCl 3 ) of compound 2k (prepared following condition A) C NMR (100 MHz, CDCl 3 ) of compound 2k (prepared following condition A) S70
71 Scanned copy of mass spectrum of 2k (prepared following condition A) S71
72 MeO Me OH 29 N Me O 1 H NMR (400 MHz, CDCl 3 ) of compound C NMR (100 MHz, CDCl 3 ) of compound 29 S72
73 Scanned copyy of mass spectrum of 29 S73
74 1 H NMR (400 MHz, CDCl 3 ) of compound (±) C NMR (100 MHz, CDCl 3 ) of compound (±)-30 S74
75 Scanned copy of mass spectrum of (±)-30 S75
76 1 H NMR (400 MHz, CDCl 3 ) of compound (±)-1b C NMR (100 MHz, CDCl 3 ) of compound (±)-1b S76
77 Scanned copy of mass spectrum of (±)-1b S77
78 1 H NMR (400 MHz, CDCl 3 ) of compound (±)-31a C NMR (100 MHz, CDCl 3 ) of compound (±)-31a S78
79 1 H NMR (400 MHz, CDCl 3 ) of compound (±)-31b 13 C NMR (100 MHz, CDCl 3 ) of compound (±)-31b S79
80 1 H NMR (400 MHz, CDCl 3 ) of compound (±)-5a C NMR (100 MHz, CDCl 3 ) of compound (±)-5a S80
81 Scanned copy of mass spectrum of (±)-5a S81
82 1 H NMR (400 MHz, CDCl 3 ) of compound (±)-5b 13 C NMR (100 MHz, CDCl 3 ) of compound (±)-5b S82
83 Scanned copy of mass spectrum of (±)-5b S83
84 H NMR (400 MHz, 0.4 ml CDCl 3, 0.1 ml DMSO-D 6 ) of compound (±)-32a 13 C NMR (100 MHz, 0.4 ml CDCl 3, 0.1 ml DMSO-D 6 ) of compound (±)-32a S84
85 H NMR (400 MHz, 0.4 ml CDCl 3, 0.1 ml DMSO-D 6 ) of compound (±)-32b 13 C NMR (100 MHz, 0.4 ml CDCl 3, 0.1 ml DMSO-D 6 ) of compound (±)-32b S85
86 Scanned copy of mass spectrum of (±)-32b S86
87 Determination of diastereomeric ratio of compound 31a from 1 H NMR of crude reaction mixture: 1 H NMR (400 MHz, CDCl 3 ) of crude reaction mixture of (±) 31a S87
88 Determination of diastereomeric ratio of compound 31b from 1 H NMR of crude reaction mixture: 1 H NMR (400 MHz, CDCl3) of crude reaction mixture of (±)-31b S88
89 Determination of diastereomeric ratio of compound 5a from 1 H NMR of crude reaction mixture: 1 H NMR (400 MHz, CDCl 3 ) of crude reaction mixture of (±)-5a S89
90 Determination of diastereomeric ratio of compound 5b from 1 H NMR of crude reaction mixture: Bn N O O N ( )-4b Bn 1 H NMR (400 MHz, CDCl3) of crude reaction mixture of (±)-4b S90
91 HPLC Traces HPLC trace of compound (± ±)-6a: H N O HO ( )-6aa NH S91
92 HPLC trace of compound (+)-6a: H N O HO ( )-6a 91% ee NH S92
93 HPLC trace of compound (±)-15a: Me N O MeO (15a ) NMe S93
94 HPLC trace of compound (+)-15a: Me N O NMe MeO ( )-15a S94
95 HPLC trace of compound (±)-9a: H N O (9a) HN S95
96 HPLC trace of compound (±)-9a synthesized from compound (+)-6a: H N O (9a) HN S96
97 HPLC trace of compound (±)-16a: Me N O (16a) Me en S97
98 HPLC trace of compound (±)-16a synthesized from compound (+)-15a: Me N O MeN (16a) S98
99 Figure: X-ray structure of compound 9g with 40% thermal ellipsoids. S99
100 S100
101 S101
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