73632251-03-retrosintesis (1)
TRANSCRIPT
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RETROSINTESIS DAN
DISKONEKSI
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Transformasi : Pengubahan yang tepatsesuai dengan yang ditargetkan dari suatu
reaksi sintesis.
Br
KOH
EtOH
2.1 2.2
OH
CrO3
O
2.3 2.4
CHO
2.5HO
CHO
2.6
1. NaOEt, EtOHrefluks
2. H3O+
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Retrosintesis, cara penyelesaian masalah
transformasi struktur dari suatu target molekul
melalui serangkaian tahapan reaksi yangakhirnya akan bermuara pada bahan awal yangsederhana atau yang dapat diperoleh denganmudah
CHO
2.5HO
CHO
2.6
a
Senyawa 2.6 dihasilkan dari 2.5
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Retrosintesis
CHO
2.5HO
CHO
2.6
1. NaOEt, EtOH
refluks
2. H3O+
CHO
2.5HO
CHO
2.6
a
Sintesis
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Retrosintesis
Spesies 2.9 dan .CO2 bukan senyawa riil, dan dinamakan
Synthon (Produk diskoneksi)
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Retrosintesis
Langkah yang harus dilakukan adalah membuka kepustakaan
tentang Transformasi Gugus Fungsi
CN Br CO2H
O
2.7
2.8
Contoh
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Diskoneksi dengan penomeran
Senyawa 2.21 telah ditentukan sebagai bahan awal dari senyawa
2.20. Kebolehjadian diskoneksi adalah 2.22 atau 2.23
O
O O
1
2.202.21
2.22 2.23
2
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Diskoneksi dengan penomeran
O2.20 2.21
O2.20O
2.242.25
+
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Diskoneksi dengan penomeran
O2.20 2.21
O2.20O
2.242.25
+
O2.20O2.26
2.27
+
Table 2.1
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Konsep HSAB (Hard/Shoft Acid/Base)
X
a
a
d d
2.28
X = halogen
a = acceptor
d = donor
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Konsep HSAB (Hard/Shoft Acid/Base)
MgBr
O
Cl
Br
O
O O2.29 2.302.31
2.32
2.33
2.34
2.35
2.36
d
aa
d
O2.20O
2.242.25
+
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Konsep HSAB (Hard/Shoft Acid/Base)
Table 2
Ekuivalensi sintetik adalah fragmen molekul yang ekivalen
dengan molekul riil berdasarkan atas keidentikkan reaktifitas
kimianya
Br
O
O2.31
2.32
2.35
2.36
a
d
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Funtional group exchange reaction wheel
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Jalur sintesis terpil ih
Br
OO2.31 2.32
2.35
2.36
a
d
Br
O
HBr
t-BuOOtBu
O
LDA, THF
-78oC
O
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Bagaimana dengan jalur diskoneksi lain?
O2.20O2.26
2.27
+
•Apa ekivalensi sintetik dari 2.26 dan 2.27 ?
•Bagaimana jalur sintesis terpilih ?
•Bandingkan kemudahan sintesis dari dua alternatif jalur sintesis
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Sintesis dengan bahan awal yang sudah diketahui
Menentukan kedudukan karbon yang terdapat pada bahan
awal yang juga terdapat pada target.Diskoneksi ikatan secara maksimum
Gunakan konsep donor-aseptor untuk mengubah hasildiskoneksi menjadi bagian nukleofilik dan elektrofilik
Tentukan pasangan intermediet ionik yang paling cocokuntuk menyempurnakan sintesis ikatan C-C yang diinginkan
Ulangi proses hingga semua ikatan karbon-karbon yangmembentuk reaksi telah ditentukan
Gunakan Pengendali reaksi perubahan gugus fungsi untukmemanipulasi/mengubah gugus fungsi dari semua hasildiskoneksi
Balikkanlah skema retrosintetik untuk menyelesaikansintesis.
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Lakukan retrosintesis dari reaksi berikut:
Analisis Retrosintesis
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Retrosintesis
Sintesis
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Retrosintesis
Sintesis
Lakukan retrosintesis dari reaksi berikut:
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Retrosintesis
Sintesis
Lakukan retrosintesis dari reaksi berikut:
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Retrosintesis
Sintesis
Lakukan retrosintesis dari reaksi berikut:
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Retrosintesis
Sintesis
Lakukan retrosintesis dari reaksi berikut:
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Retrosintesis
Lakukan retrosintesis dari reaksi berikut:
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Sintesis
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Retrosintesis
Lakukan retrosintesis dari reaksi berikut:
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Sintesis
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Contoh Soal
O
O
8.56
C-O
n-C5H11Br
O
OH
CH2O
HO
Br
(8.56)
eter
+
+++ CO2
Analisis
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Contoh Soal
Sintesis
Br
1. Mg
2. CH2O
HO
(67%)
1. basa
2. C5H11Br
1. Na
2. CO2
O
O
+
HOO
O
H+