Organic synthesis

1
?????
????

• ? ? ? ?
• Organic synthesis

2
??????????
???????????????????????
????????????
??????????????????,???? ??????
???? ????
??????????,????????????

??????????????????????
??,???????????
????????????????,???
C60,C70
3
???? ??6000?????,?????????? ? ? ? ? ???
? ? ? ? ??????????? ? ????????????
???????????????????????? ? Woodward . R . B
(1965) Vitamin B12 -VB12 (1973)

Erythonolide (???A) (1981) Corey . E .
J . (1990) PGF2a PGE2 Nicolaou .
K . C Taxol (???)(1994).
Brevetoxinl ???????? ???????????????.
? ?
4
??????????????????,????? (?68?????)???????
??? (1994 . Y .Kishi), ???????,??????????????????
????????? ???????.
5

• ?????????
• 1? ??? (????????????????)
• 2???? (????,????)
• 3???????
• 4????????????
• 5 ???????? ?????, ????
• 
  ?,???????

6
????????????????
??? ??????
???????? ????
????
?????????? ???????(????? ???)
?????????(?????????????) ?
?????????? (? ?)
7
1??????( ????????????) ?????
???,?????? ?????
? ? ? ?
???? ????
(??) (??)
? ? ? ? ?????????
8
??????C-C???? (1)????? ????(????)???????????
??? ?????(????,????) ?
???? RMgBr ??? RLi ????
R2CuLi ????? RC?C- MgX(Na)
9
????a-??? H ????? ??????????
10
?????????????,???? a-H????,???????
11
(No Transcript)
12
???? C-C ????
(1)?????
13
(2)?????????????
14
(No Transcript)
15
(No Transcript)
16
????????
17
2??????
(1)???
(2)????? (3)????? (4)?????
18
3???
(1)??(?)??
3?
4?
19
??
??
20
4?????
(1)?Pinacol??
(2)?Beckmann??
21
?????????????????? ????????????????????? ???,????
????????????? (Comprehensive Organic
Transformations)
1??????? ????????????????????
22
?????????????-??????
23
(No Transcript)
24
2??????????
??
25
??
26
(No Transcript)
27
????????
?????????????
1???
2.??
28
3?????
?? ??
29
(No Transcript)
30
4?????
31
4????? (1)?????
(2)??????
32
???????????
(??? ? ?????(?????,???) ?????? ???
????(retro synthesis)
a??b
33
??????????????, ???????,?????????
??????????????,??? ??????,?????????? ?
?
b??,a???
?
b??a
??????
34
???????????
1. ß-??(? a ?ß??? )????????
35
2. 1,3-?????????
36
3. 1,5-?????????
37
(No Transcript)
38
4. 1,4 ? 1,6-?????????
39
(No Transcript)
40
5. a-??????????
41
?. ????????????
??????
42
1?????
43
(No Transcript)
44
2???????
45
3??????????
46
??????
??????????? ? ???? ? ??????????????????????? ?
??????????????????
47
???????????
1. ?(?)???.
(1). ??
(2). ??
(3).
48
(4).
??????? ??????
2?????
49
3??(?)???
4?????
50
The End of Chapter 22
Thanks for Your Attention