Supporting Information
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- Ματθαίος Κυπραίος
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1 Supporting Information Biomimetic total syntheses of borreverine and flinderole alkaloids. Dattatraya. Dethe,* Rohan D. Erande and Alok Ranjan Department of Chemistry, Indian Institute of Technology-Kanpur, Kanpur , India. Tel: , fax:
2 Table of Contents: MR data comparisons of isoborreverine (5):...3 MR data comparisons of dimethylisoborreverine (6):...4 MR data comparisons of flinderole A (1):...5 MR spectra of compound 22, 22a, 19, 24, 25a, 25b, 25c, 25 and 23a:...6 OESY of compound 23a:...18 MR spectra of compound 23b:...19 Crystal structure of compound (23b):...20 CIF file of compound (23b):...21 MR spectra of comp. 26, 27, 28a, 28b, 34, 35, 36, 38, 32, 39a, 39b, 40a, 40b and 45:...22 MR spectra of dimethylisoborreverine (6) in DMSO-d 6 :...41 MR spectra of dimethylisoborreverine (6) in CDCl 3 :...42 MR spectra of TFA salt of dimethylisoborreverine (6) in DMSO-d 6 : MR spectra comparisons of dimethylisoborreverine (6): C MR spectra comparisons of dimethylisoborreverine (6):...45 MR spectra of TFA salt isoborreverine (5):...46 MR spectra of isoborreverine (5) in DMSO-d 6 : MR spectra comparisons of isoborreverine (5): C MR spectra comparisons of isoborreverine (5):...49 MR spectra of isoborreverine (5) in CDCl 3 :...50 MR spectra of compound 46a:...51 MR spectra of flinderole A (1): MR spectra comparisons of flinderole A (1): MR spectra comparisons of TFA salt flinderole A (1): C MR spectra comparisons of TFA salt flinderole A (1):...56 MR spectra of compound 46b:...57 MR spectra of desmethyl flinderole (C):...58 MR spectra comparisons of desmethyl flinderole (C):...60 MR spectra of compound 48, 49, 50, 51, 52, 53, 10, 54a and 54:
3 C atural isoborrevrine F. Tillequin, M. Koch J. at. Prod., 48, 120 (1985). atural isoborreverine A. M. Balde et al., Phytochemistry, 15, 997 (1991). Synthetic isoborrevrine Position δc (CDCl 3, 20 Mz) δc (CDCl 3, Mz) δc (CDCl 3, 100 Mz)
4 ' 17' ' 4' 12 16' 6' 11' 9' Dimethyl isoborreverine (6) atural dimethyl isoborreverine (DMSO-d 6 ) Synthetic dimethyl isoborrevrine (DMSO-d 6 ) atural dimethyl isoborrevrine (DMSO-d 6 ) Synthetic dimethyl isoborrevrine (DMSO-d 6 ) Liza Sylvia Fernandez, Griffith University, Ph.D. thesis, (2009) Liza Sylvia Fernandez, Griffith University, Ph.D. thesis, (2009) Position δc (150 Mz) (Chemical shifts determined from 2D MR experiments) δc (125 Mz) δ (600 Mz) (mult, J z) δ (500 Mz) (mult, J z) 1 () (brs) (brs) (d, 9.0) 5.49 (d, 9.5) 4 () 9.90 (brs) (brs) 4 Me (m)a, 3.35 (m)b 3.33 (m)a, 3.34 (m)b , , (d, 7.8) 7.67 (d, 7.6) (dd, 7.8, 7.8) 7.02 (dd, 7.6, 7.0) (dd, 7.8, 7.8) 7.09 (dd, 7.6, 7.3) (d, 7.8) 7.28 (d, 7.9) (m) 3.14 (m) (s) 0.69 (s) (s) 1.04 (s) (m) 4.11 (m) 4 () 9.79 (brs) (brs) 4 Me (m)a, 3.35 (m)b 3.33 (m)a, 3.34 (m)b , , (d, 7.8) 7.52 (d, 7.9) (dd, 7.8, 7.8) 6.88 (dd, 7.3, 7.3) (dd, 7.8, 7.8) 6.71 (dd, 7.6, 7.3) (d, 7.8) 6.22 (d, 7.9) (brm) 5.46 (brm) , (m), 2.28 (d, 17.4) 1.72 (m), 2.28 (d, 14.0) (brs) 1.69 (brs) 4
5 atural Flinderole A (TFA salt in DMSO-d 6 ) Synthetic Flinderole A (TFA salt in DMSO-d 6 ) atural Flinderole A (TFA salt in DMSO-d 6 ) Synthetic Flinderole A (TFA salt in DMSO-d 6 ) V. M. Avery et al., Org. Lett., 11, 329 (2009). V. M. Avery et al., Org. Lett., 11, 329 (2009). Position δc (150 Mz) (Chemical shifts determined from 2D experiments) δc (125 Mz) δ (600 Mz) (mult, J z) δ (500 Mz) (mult, J z) 1 () (s) (s) (d, 16.2) 6.58 (d, 16.3) 4 () 8.60 (m)a 8.84 (m)a 8.54 (m)b 8.78 (m)b 4 Me (t, 5.4) 2.62 (t, 5.4) (m, 2) d 2.99 (m, 2) d b 20.2 b 3.01 (m)a e 3.01 (m)a e 2.90 (brt, 7.5)b f 2.90 (brt, 8.0)b f c c 7.53 (brd, 7.5) 7.54 (brd, 8.0) (dd, 7.5, 7.5) 6.98 (dd, 7.4, 7.4) (dd, 7.5, 7.5) 7.08 (dd, 7.7, 7.7) (brd, 7.5) 7.25 (brd, 7.7) (dd, 13.2, 8.0)β f 2.90 (dd, 12.9, 8.0)β f 2.31 (dd, 13.2, 7.5)α 2.31 (dd, 12.6, 7.7)α (d, 16.2) 6.52 (d, 16.3) (s) 1.96 (s) (ddd, 9.6, 8.0, 7.5) 4.30 (ddd, 8.9, 8.3, 8.0) 4 () 8.48 (m, 2) 8.78 (m, 2) 4 Me (brt, 5.4) 2.56 (brt, 5.2) (m, 2) d 2.99 (m, 2) d b 20.3 b 3.01 (m) a e 3.01 (m) a e 2.90 (brt, 7.5)b f 2.90 (brt, 8.0)b f c c 7.56 (d, 7.5) 7.58 (d, 7.7) (dd, 7.5, 7.5) 7.02 (dd, 6.3, 6.3) (dd, 7.5, 7.5) 7.04 (dd, 6.3, 6.3) (d, 7.5) 7.43 (d, 7.4) (dsept., 9.6, 1.3) 5.32 (dsept., 8.9, 1.2) (d, 1.3) 1.85 (d, 1.3) (d, 1.3) 1.80 (d, 1.3) 5
6 RPALC_1-4.JDF O SO 2 Ph RPALC_13C-3.JDF CLOROFORM-d O SO 2 Ph
7 TMS CLOROFORM-d
8 TMS
9 CLOROFORM-d
10 R732_11O_E14.ALS R732_13C-2.JDF ACETOITRILE-d3 ACETOITRILE-d
11 Wed2av400# r.esp TMS Sat2av2# r.esp CLOROFORM-d
12 Tue4av2# r.esp TMS Fri4av2# r.esp CLOROFORM-d
13 Wed4av400# r.esp CLOROFORM-d TMS Fri4av2# r.esp CLOROFORM-d
14 Fri4av2# r.esp Wed4av2# r.esp TMS
15 Sat4av2# r.esp CLOROFORM-d Sat4av2# r.esp
16 Thu3av400# r.esp TMS Fri1av2# r.esp
17 Fri1av2# r.esp
18 18
19 Thu3av400# r.esp CLOROFORM-d 2O TMS CO 2 Et 19b Fri3av400# r.esp CLOROFORM-d CO 2 Et 19b
20 Fri3av400# r.esp CO 2 Et 19b
21 21
22 Tue2av400# r.esp TMS O Fri2av2# r.esp CLOROFORM-d
23 Fri2av2# r.esp O Mon3av400# r.esp CLOROFORM-d 2O TMS
24 Mon3av2# r.esp CLOROFORM-d Mon3av2# r.esp
25 Fri3av2# r.esp CLOROFORM-d 2O TMS Sat3av2# r.esp CLOROFORM-d
26 Sat3av2# r.esp Wed4av400# r.esp CLOROFORM-d 2O TMS O 24b
27 Sat4av2# r.esp CLOROFORM-d O 24b
28 CLOROFORM-d
29 R680_1-4.esp CO 2 Me R680_13C-3.JDF CLOROFORM-d CO 2 Me
30 R680_DEPT135-5.JDF CO 2 Me 31 R681_1-4.JDF CO 2 Me 32 Br
31 R681_13C-3.JDF CLOROFORM-d CO 2 Me 32 Br R681_DEPT135-5.JDF CO 2 Me 32 Br
32 R682_1-12.JDF Water DMSO R682_13C-4.JDF DMSO-d
33 R682_DEPT135-5.JDF DMSO-d R653_1-4.JDF 2O
34 R653_13C-2.JDF ACETOITRILE-d3 ACETOITRILE-d R653_DEPT135-3.JDF
35 RFIALA_1_1-4.JDF 2O ACETOITRILE-d RFIALA_13C-5.JDF ACETOITRILE-d3 ACETOITRILE-d
36 RFIALA 135DEPT-5.JDF RFID_1-4.JDF 2O ACETOITRILE-d
37 RFID_13C-7.JDF ACETOITRILE-d3 ACETOITRILE-d O O 35b R487_1-12.JDF ACETOITRILE-d
38 R487_13C-3.JDF ACETOITRILE-d3 ACETOITRILE-d R_FIALC_1-4.JDF O 36b O
39 RFIALC_13C-2.JDF CLOROFORM-d O 36b O RFIALC_135DEPT-3.JDF
40 R668_1-8.JDF 2O ACETOITRILE-d O O R_668_13C-3.JDF ACETOITRILE-d3 ACETOITRILE-d O O
41 R616_1-4.JDF R616_13C-2.JDF DMSO-d
42 R718_1-4.JDF CLOROFORM-d R718_13C-3.JDF CLOROFORM-d Dimethyl isoborreverine (6) CDCl 3, 125 Mz
43 R716TFA_1-4 (1).JDF TFA salt of synthetic Dimethyl isoborreverine (6) 500 Mz, DMSO-d6 R716TFA_13C-6.JDF
44 Jeremy A. May et.al. JACS 2012 R616_1-4.JDF Synthetic Dimethyl isoborreverine (6) 500 Mz, DMSO-d6 44
45 Jeremy A. May et.al. JACS 2012 MR Solvent: CDCl 3 R718_13C-3.JDF
46 ARD29_1-10.JDF TFA salt of synthetic Isoborreverine (5) 500 Mz, DMSO-d ARD30_13C-3.JDF DMSO-d TFA salt of synthetic Isoborreverine (5) 125 Mz, DMSO-d
47 ARD22_1-6.JDF 2O Synthetic Isoborreverine (5) 500 Mz, DMSO-d ARD24_13C-2.JDF DMSO-d Synthetic Isoborreverine (5) 125 Mz, DMSO-d
48 Jeremy A. May et. al. JACS 2012 DMSO d6 ARD29_1-10.JDF
49 Jeremy A. May et. Al. JACS 2012 DMSO d6 ARD24_13C-2.JDF synthetic Isoborreverine (5) 125 Mz, DMSO-d
50 CLOROFORM-d Synthetic Isoborreverine (5) 400 Mz, CDCl CLOROFORM-d Synthetic Isoborreverine (5) 100 Mz, CDCl
51 R32PDIALDEYDE_1-4.JDF 2O O 42a O R3+2PDIALDEYDE_13C-1.JDF ACETOITRILE-d3 ACETOITRILE-d O 42a O
52 EPIFIALA_1-4.JDF 2O DMSO-d EPIFLIDA_13C-2.JDF DMSO-d
53 EPIFLIDA_DEPT135-4.JDF DMSO-d Synthetic Flinderole A (1) 125 Mz, DMSO-d
54 Jeremy A. May et.al. JACS 2012 DMSO d6 EPIFIALA_1-4.JDF Synthetic Flinderole A (1) 500 Mz, DMSO-d 6 54
55
56
57 R657_1-4.JDF 2O CLOROFORM-d Grease O O 42b R657_13C-2.JDF CLOROFORM-d Graese O 42b O
58 R637_DEPT135-4.JDF Grease O b O RFLIDA_1-19.JDF DMSO-d
59 REPIFLIDA_13C-3.JDF DMSO-d RFLIDA_DEPT135-4.JDF DMSO-d
60 Jeremy A. May et.al. JACS 2012 RFLIDA_1-19.JDF Synthetic Desmethyl Flinderole C 500 Mz, DMSO-d6 60
61 ARD10_1-4.JDF ARD1013_13C-1.JDF CLOROFORM-d
62 ARD1013_DEPT135-3.JDF ARD31_1-4.JDF
63 ARD31_13C-1.JDF CLOROFORM-d ARD41_1-4.JDF
64 ARD38_13C-3.JDF CLOROFORM-d ARD38_135DEPT-4.JDF
65 ARD42_1-8.JDF CLOROFORM-d ARD42_13C-2.JDF CLOROFORM-d
66 ARD42_135DEPT-3.JDF ARD48_1-5.JDF CO 2 Et SO 2 Ph
67 ARD20_13C-4.JDF CLOROFORM-d ARD20_DEPT135-5.JDF
68 ARD50_1-4.JDF ARD50_13C-2.JDF ACETOITRILE-d3 ACETOITRILE-d
69 ARD50A_DEPT135-3.JDF ARD34_1-4.JDF CLOROFORM-d grease
70 ARD44_13C-1.JDF CLOROFORM-d ARD44_DEPT135-3.JDF
71 ARD12_1-4.JDF CLOROFORM-d DCM ARD121_13C-2.JDF CLOROFORM-d
72 R637B_1-4.JDF CLOROFORM-d R637B_13C-2.JDF CLOROFORM-d
73 R637B_DEPT135-3.JDF
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