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Nature Chemistry 2011-2015
Gaich Group Seminar, Christa Gerlinger, August 3, 2016
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Overview 2011-2015
1
Total Syntheses and Methodologies
Gaich Group Seminar, Christa Gerlinger, 03.08.16
2011 2012 2013
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Overview 2011-2015
2
2014
Total Syntheses and Methodologies
2015
Gaich Group Seminar, Christa Gerlinger, 03.08.16
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Nat. Chem. 2011, 3, 449.
(±)-Conolidine - Micalizio
Gaich Group Seminar, Christa Gerlinger, 03.08.16
3
Key features:
- [2,3]-Wittig rearrangement
- Nucleophilic addition
- Cyclization
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Gaich Group Seminar, Christa Gerlinger, 03.08.16
4 Nat. Chem. 2011, 3, 449.
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Loline alkaloids - Trauner
Gaich Group Seminar, Christa Gerlinger, 03.08.16
5
Key features:
-Sharpless epoxidation
- Grubbs olefin metathesis
-transannular/deoxycarbonylative aminobromination
Nat. Chem. 2011, 3, 543.
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Gaich Group Seminar, Christa Gerlinger, 03.08.16
6 Nat. Chem. 2011, 3, 543.
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Hyperpapuanone, Hyperibone L, epi-Clusianone, Oblongifolin A - Plietker
Gaich Group Seminar, Christa Gerlinger, 03.08.16
7 Nat. Chem. 2011, 3, 938.
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Gaich Group Seminar, Christa Gerlinger, 03.08.16
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a) NaH (1.1 equiv), R1X (1.5 equiv), EtOH, 0 °C to rt, 15 h, then K2CO3 formaldeyde, rt b) MeMgCl (2 equiv), dimethyl 1,3-acetonedicarboxylate (1 equiv),
MeOH, 0 to 60 °C, 15 h, c) NaH (1.1 equiv), MeLi (2.3 equiv). THF, 0 °C, 5 h, d) NaH (1.1 equiv), 18-crown-6 (0.1 equiv), R2X (1.5-2.5 equiv), THF, 0 °C to
rt, 15 h,
Nat. Chem. 2011, 3, 938.
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Gaich Group Seminar, Christa Gerlinger, 03.08.16
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e) LiCl (2.02 equiv), CuI (2 equiv), MeMgBr (2equiv), Me3SiCl (2 equiv), THF, -78 °C, 5 h, f) KO-t-amylate (2 equiv), 1,3-dimesitylimidazolin-2-ylidene
hexafluorophosphat (0.1 equiv), Bu4N[Fe(CO)3(NO)] (0.1 equiv) , 2-methyl-3-butene-2-yl methylcarbonate (2 equiv), THF/MTBE, 0 to 80 °C, 20 h, f) KH
(1.1 equiv), 18-crown-6 (0.1 equiv), MeI (2 equiv), dimethoxyethane, 0 °C to rt, 15 h
Nat. Chem. 2011, 3, 938.
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g) KOtBu (2 equiv), R4-C(=CO)CN (3.3 equiv), THF, 0 to 35 °C, 24 h
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2011, 3, 938.
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11
Taxanes - Baran
Gaich Group Seminar, Christa Gerlinger, 03.08.16
Key features:
- 1,6-addition
- Mukaiyama aldol reaction
- Diels-Alder reaction
Nat. Chem. 2012, 4, 21.
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12 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2012, 4, 21.
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13
Decarboxylative allylic alkylations of lactams - Stoltz
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2012, 4, 130.
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14 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2012, 4, 130.
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15 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2012, 4, 130.
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Au-catalysed enantioselective cope-rearrangement of achiral 1,5-dienes– Gangé
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2012, 4, 405.
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17
Daphenylline - Li
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2013, 5, 679.
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18 Gaich Group Seminar, Christa Gerlinger, 03.08.16
Nat. Chem. 2013, 5, 679.
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19 Gaich Group Seminar, Christa Gerlinger, 03.08.16
Nat. Chem. 2013, 5, 679.
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Enantioselective silyl protection of alcohols - Snapper
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2013, 5, 768.
Features:
-lower catalyst loadings and reaction temperatures
- shorter reaction times
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Construction of contiguous all-carbon qc stereocentres - Ooi
Gaich Group Seminar, Christa Gerlinger, 03.08.16
Ligand (114)
Nat. Chem. 2014, 6, 47.
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22
Aromatic ene reaction - Hoye
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2014, 6, 34.
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23 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2014, 6, 34.
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24 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2014, 6, 34.
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Biogenetically inspired synthesis of indole alkaloids - Oguri
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2014, 6, 57.
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26 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2014, 6, 57.
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27 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2014, 6, 57.
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Epicolactone - Trauner
Gaich Group Seminar, Christa Gerlinger, 03.08.16
Key features:
-[5+2] cyclo-addition
- lactone formation
- vinylogue aldol addition
Nat. Chem. 2015, 7, 879.
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Possible mechanism
Epicolactone (168)
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2015, 7, 879.
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(-)-jiadifenolide - Shenvi
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2015, 7, 604.
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31 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2015, 7, 604.
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Addition of Gignard reagents to α–epoxy N-sulfonyl hydrazones - Coltart
Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2015, 7, 1024.
Proposed mechanism:
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33 Gaich Group Seminar, Christa Gerlinger, 03.08.16 Nat. Chem. 2015, 7, 1024.
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Thank you!
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