total synthesis of tetraketide and cryptorigidifoliol i ... · pdf filer e tz aly ion...
TRANSCRIPT
Total Synthesis of Tetraketide and Cryptorigidifoliol I
via a Sequential Allylation Strategy
Birakishore Padhi,†,‡ G. Sudhakar Reddy,†,‡ and Debendra K. Mohapatra*,†,‡
†Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology
Hyderabad 500 007, India
‡Academy of Scientific and Innovative Research, New Delhi, 110025, India
* Corresponding author. Tel.: +91-40-27193128; fax: +91-40-27160512
OO
O
14
OH OO
O
Au
Mg
Au
Ti
TiReetz allylation
Diastereoselective allylation
Mitsunobu lactonization
Mitsunobu lactonization Reetz allylation
Diastereoselective allylation
Maruoka allylation
Sakurai allylation
Tetraketide (1) Cryptorigidifoliol I (2)
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S2
Table of Contents
Ser. No. Description Page No.
1 1H and 13C NMR Copy of 20 S4 S5
2 1H and 13C NMR Copy of 21 S6 S7
3 HPLC of Chromatogram of 21 S8 S9
4 1H and 13C NMR Copy of 22 S10 S11
5 1H and 13C NMR Copy of 23 S12 S13
6 1H and 13C NMR Copy of 13 S14 S15
7 1H and 13C NMR Copy of 24 S16 S17
8 1H and 13C NMR Copy of 12 S18 S19
9 1H and 13C NMR Copy of 1 S20 S21
9 1H and 13C NMR Copy of 18 S22 S23
10 1H and 13C NMR Copy of 28 S24 S25
11 1H and 13C NMR Copy of 29 S26 S27
12 HPLC Chromatogram of 29 S28 S29
13 1H and 13C NMR Copy of 31 S30 S31
14 1H and 13C NMR Copy of 32 S32 S33
1H and 13C NMR Copy of 32 S34 S35
16 HPLC Chromatogram of 33 S36 S37
17 1H and 13C NMR Copy of 34 S38 S39
18 1H and 13C NMR Copy of 35 S40 S41
19 1H and 13C NMR Copy of 36 S42 S43
20 1H and 13C NMR Copy of 17 S44 S45
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S3
21 1H and 13C NMR Copy of 37 S46 S47
22 HPLC Chromatogram of 37 S48 S49
23 1H and 13C NMR Copy of 16 S50 S51
24 1H and 13C NMR Copy of 15 S52 S53
25 1H and 13C NMR Copy of 2 S54 S55
26 HRMS (ESI) copy of 2 S56
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S4
1H NMR Spectrum of 20 (500 MHz, CDCl3)
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S5
13C NMR Spectrum of 20 (100 MHz, CDCl3)
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S6
1H NMR Spectrum of 21 (400 MHz, CDCl3)
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S7
13C NMR Spectrum of 21 (125 MHz, CDCl3)
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S8
HPLC Chromatogram of 21
OHOBn
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S9
LC-MS Chromatogram of 21
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S10
1H NMR Spectrum of 22 (500 MHz, CDCl3)
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S11
13C NMR Spectrum of 22 (75 MHz, CDCl3)
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S12
1H NMR Spectrum of 23 (500 MHz, CDCl3)
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S13
13C NMR Spectrum of 23 (125 MHz, CDCl3)
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S14
1H NMR Spectrum of 13 (400 MHz, CDCl3)
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S15
13C NMR Spectrum of 13 (125 MHz, CDCl3)
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S16
1H NMR Spectrum of 24 (300 MHz, CDCl3)
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S17
13C NMR Spectrum of 24 (75 MHz, CDCl3)
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S18
1H NMR Spectrum of 12 (500 MHz, CDCl3)
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S19
13C NMR Spectrum of 12 (125 MHz, CDCl3)
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S20
1H NMR Spectrum of 1 (300 MHz, CDCl3:C6D6 = 1:1)
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S21
13C of NMR Spectrum 1 (100 MHz, CDCl3:C6D6 = 1:1)
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S22
1H NMR Spectrum of 18 (300 MHz, CDCl3)
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S23
13C NMR Spectrum of 18 (100 MHz, CDCl3)
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S24
1H NMR Spectrum of 28 (500 MHz, CDCl3)
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S25
13C NMR Spectrum of 28 (125 MHz, CDCl3)
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S26
1H NMR Spectrum of 29 (400 MHz, CDCl3)
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S27
13C NMR Spectrum of 29 (100 MHz, CDCl3)
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S28
HPLC Chromatogram of 29
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S29
LC-MS Chromatogram of 29
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S30
1H NMR Spectrum of 31 (400 MHz, CDCl3)
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S31
13C NMR Spectrum of 31 (100 MHz, CDCl3)
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S32
1H NMR Spectrum of 32 (400 MHz, CDCl3)
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S33
13C NMR Spectrum of 32 (125 MHz, CDCl3)
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S34
1H NMR Spectrum of 33 (400 MHz, CDCl3)
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S35
13C NMR Spectrum of 33 (125 MHz, CDCl3)
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S36
HPLC Chromatogram of 33
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S37
LC-MS Chromatogram of 33
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S38
1H NMR Spectrum of 34 (400 MHz, CDCl3)
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S39
13C NMR Spectrum of 34 (125 MHz, CDCl3)
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S40
1H NMR Spectrum of 35 (500 MHz, CDCl3)
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S41
13C NMR Spectrum of 35 (75 MHz, CDCl3)
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S42
1H NMR Spectrum of 36 (400 MHz, CDCl3)
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S43
13C NMR Spectrum of 36 (75 MHz, CDCl3)
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S44
1H NMR Spectrum of 17 (400 MHz, CDCl3)
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S45
13C of 17 (75 MHz, CDCl3)
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S46
1H NMR Spectrum of 37 (400 MHz, CDCl3)
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S47
13C NMR Spectrum of 37 (75 MHz, CDCl3)
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S48
HPLC Chromatogram of 37
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S49
LC-MS Chromatogram of 37
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S50
1H NMR Spectrum of 16 (400 MHz, CDCl3)
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S51
13C NMR Spectrum of 16 (100 MHz, CDCl3)
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S52
1H NMR Spectrum of 15 (500 MHz, CDCl3)
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S53
13C NMR Spectrum of 15 (125 MHz, CDCl3)
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S54
1H NMR Spectrum of 2 (500 MHz, CDCl3)
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S55
13C NMR Spectrum of 2 (125 MHz, CDCl3)
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S56
HRMS(ESI) Chromatogram of 2