(Translated by https://www.hiragana.jp/)
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y 8 Chemical Interpretation is not possible for this label C Total Synthesis of Yuzurine-type Alkaloid Daphgraciline `3 l* 5
z 8 Chemical Interpretation is not possible for this label ` Li, L.-X.; Min, L.; Yao, T.-B.; Ji, S.-X.; Qiao, C.; Tian, P.-L.; Sun, J.; Li, C.-C.
F = `I eB
{ 8 Chemical Interpretation is not possible for this label h J. Am. Chem. Soc. 2022, 144, 18823 18828 ` @ :$Y 7 :$Y 9R F0
8 Chemical Interpretation is not possible for this label 9 Y
1) TsCl, NEt3, DCM, 80%
2) TIPSOTf, 2,6-Lutidin, DCM, 96% 3! Z f Z̬f
8 Chemical Interpretation is not possible for this label 8 V n P ; = O P u v ` ` ` ` 3i)DIBAL, DCM, -78 C
ii) TBSCl, imidazole, 0 C, 93%
4i) nBuLi (1 eq.), THF -78 C
ii) BOMCl, THF, 25 C
iii) nBuLi (1 eq.), THF -78 C
iv) CH2O(g), -78 C, THF, 73% f B f B f 0
8 Chemical Interpretation is not possible for this label # A+B eF ( 9 (
8 Chemical Interpretation is not possible for this label ( = X 6 7 K L c ` 8) quinidine (50 mol%), DCM, 25 C, 71%
9) TBAF, THF, -20 C
10) DMP, NaHCO3, DCM, 0 C
11) [Rh(PPh3)3Cl] (2 eq.), toluene, 120 C,
sealed tube, 60% (3 steps) fF B[ 2S B[2S t
8 Chemical Interpretation is not possible for this label " ` 12) ?
13) ? g{) 3r) 3l
8 Chemical Interpretation is not possible for this label
0 E a `
` & ` S b U ` l 14) K2OsO4, NMO, MeSO2NH2, THF/tBuOH/H2O, 25 C
15) IBX, DMSO, 25 C
16) 5.5 M KOH, tBuOH, 90 C
17) TMSCHN2, toluene/MeOH 10:1, 25 C, 45% (4 steps) gK) A) gƝ
; 8 Chemical Interpretation is not possible for this label ; \ Q & ' 18i) NaH (25 eq), THF, 0 C
ii) CS2 (35 eq), THF, 0 C
iii) MeI (40 eq), THF, 25 C
19) chlorobenzene, 148 C, 92% (2 steps)
20) SmI2, THF, 25 C, 85%
21i) DIBAL (5 eq), DCM, -78 C
ii) TIPSCl, imidazole, DCM 0 - 25 C, 64% (2 steps) @ $ 33 $ f
8 Chemical Interpretation is not possible for this label 3 d
` 22i) Li, EtNH2(l), -78 C
ii) EtOH, MeI, 25 C
23) KHMDS, Ts-imidazole, THF, 0 C, 40% (2 steps) f b fFb f6j
8 Chemical Interpretation is not possible for this label E ]
` ( a ) ` 24i) [TiCp2Cl2], Zn, THF, 25 C
ii) H, malononitrile, THF, 70 C
iii) H2O, 70 C, 81% fB 2
B28
8 Chemical Interpretation is not possible for this label
F Z ` $ b % ` k 25) EtMgBr (1 eq), Et2O, -78 C
26) pTsOH, MeOH, 25 C, 62% (2 steps)
27) DMP, DCM, 25 C
28) MeOH, KOH, I2, 0 C, 79% (2 steps) + 2ы eы9,]
9 8 Chemical Interpretation is not possible for this label
5 a x ` ` ` ` > ? ` e b f ` 29i) TPP, O2, hn, CDCl3, -55 C
ii) P(OEt)3, 70%
30) MgSO4, 1,2-Dichlorobenzene, 140 C, 83%
31) pTsOH, THF/H2O, 80% 3 f¼ fF¼f
> 8 Chemical Interpretation is not possible for this label daphgraciline fW` fFN`fZxf
A 8 Chemical Interpretation is not possible for this label
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D 8 Chemical Interpretation is not possible for this label
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% & J K c ` k 5) DIAD, PPh3, THF, 0 - 25 C 73%
6) pTsOH (10 mol%), MeOH, 0 C, 70%
7i) mCPBA, DCM, 0 C
ii) Ac2O, NEt3, DCM, 0 C, 85% ' D @Y @Y
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