(Translated by https://www.hiragana.jp/)
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8 Chemical Interpretation is not possible for this label m Synthesis of Eupalinilide E, a Promoter of Human Hematopoietic Stem and Progenitor Cell Expansion m Synthesis of Eupalinilide E, a Promoter of Human Hematopoietic Stem and Progenitor Cell Expansion w7, ƓY $ 6 ww. V
8 Chemical Interpretation is not possible for this label P Johnson, T.C., Chin, M.R., Han, T., Shen, J.P., Rana, T., Siegel, D. P Johnson, T.C., Chin, M.R., Han, T., Shen, J.P., Rana, T., Siegel, D.
ݝ: ƓY CD2 v < #
8 Chemical Interpretation is not possible for this label i J. Am. Chem. Soc., 2016, 138, 18, 60686073 i J. Am. Chem. Soc., 2016, 138, 18, 60686073 ^ DP j zH j B
$ 8 Chemical Interpretation is not possible for this label % : O \ ' ) - . 2 3 1. HBr, AcOH, 0 C
2. Br2, AcOH, RT
3. i-PrNH2, Et2O, RT
4. AcOH, THF, 50 C
50% (4 steps) ( * . / 3 4 1. HBr, AcOH, 0 °C
2. Br2, AcOH, RT
3. i-PrNH2, Et2O, RT
4. AcOH, THF, 50 °C
50% (4 steps) m D M M! }
J 8 Chemical Interpretation is not possible for this label
( O t } ~ 9. i. (H2C=CH)4Sn, n-BuLi, THF, -78 C
ii. propargyl bromide, HMPA, THF,
-78 C to RT, 81% (2 steps)
10. TMSCl, n-BuLi, THF, -78 C, 99% 9. i. (H2C=CH)4Sn, n-BuLi, THF, -78 °C
ii. propargyl bromide, HMPA, THF,
-78 °C to RT, 81% (2 steps)
10. TMSCl, n-BuLi, THF, -78 °C, 99% q e1 Ci e1v
} 8 Chemical Interpretation is not possible for this label 1 w
! 5. LiAlH4, Et2O, 0 C, 99%
6. Ac2O, 150 C, 91% y
! " 5. LiAlH4, Et2O, 0 °C, 99%
6. Ac2O, 150 °C, 91% _ r wW r- 6^
~ 8 Chemical Interpretation is not possible for this label
! 2 B
- . 7. LiAlH4, Et2O,
0 C, 49%
8. DMP, NaHCO3,
DCM, RT, 87%
. / 7. LiAlH4, Et2O,
0 °C, 49%
8. DMP, NaHCO3,
DCM, RT, 87% ; f L&
8 Chemical Interpretation is not possible for this label
/ B ^ 5 6 12. (COCl)2, DMSO, Et3N,
DCM, -78 C
13. Et2AlCl, DCM,
-78C, 99% (2 steps) 6 7 12. (COCl)2, DMSO, Et3N,
DCM, -78 °C
13. Et2AlCl, DCM,
-78°C, 99% (2 steps) F s@* ffk@* 3
8 Chemical Interpretation is not possible for this label > T v Z [ 14. tiglic acid, 2,4,6-TCBC, Et3N, DMAP, toluene, 80 C, 90%
15. TFA, DCM, RT, 98%
16. CrO3, 3,5-DMP, DCM, 0 C, 36% [ \ 14. tiglic acid, 2,4,6-TCBC, Et3N, DMAP, toluene, 80 °C, 90%
15. TFA, DCM, RT, 98%
16. CrO3, 3,5-DMP, DCM, 0 °C, 36% M V fV u5
8 Chemical Interpretation is not possible for this label 1 d 17. Yb(OTf)3, NaBH4,
MeOH/THF, -78C, 75% e 17. Yb(OTf)3, NaBH4,
MeOH/THF, -78°C, 75% ' ' ̌ B
8 Chemical Interpretation is not possible for this label + (R)-carvone + (R)-carvone na nǎ
8 Chemical Interpretation is not possible for this label eupalinilide E eupalinilide E >+
8 Chemical Interpretation is not possible for this label
9 Z m C D E F 11. i. Pd(OAc)2, B2pin2,
MeOH, toluene, 50 C
ii. H2O2, NaOH, THF, 0 C
62% (2 steps) D E F G 11. i. Pd(OAc)2, B2pin2,
MeOH, toluene, 50 °C
ii. H2O2, NaOH, THF, 0 °C
62% (2 steps) ffN)/
8 Chemical Interpretation is not possible for this label
3 M i
18. Al(O sec-Bu)3, TBHP,
DCM, 0 C to RT
19. LiCl, HCl, THF, RT,
23 C, 86% (2 steps)
18. Al(O sec-Bu)3, TBHP,
DCM, 0 °C to RT
19. LiCl, HCl, THF, RT,
23 °C, 86% (2 steps) $ iN V
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