Page 389 - Advanced Organic Chemistry Part B - Reactions & Synthesis

(a) CH CH CH OH (b) H 361
2 2 2
O CH 3 CONHBr
N O C H BrO
I , NaHCO 3 7 9 4 PROBLEMS
2
C H NO I H 2 O
10 14 3 OH
H
CH 3 O 2 C
(c) 1) Hg(O SCF ) (d) CH
3 3 2 3 I , KI
CH CN CO H 2
) C(CH ) CH CH 3 C H OClHg 2 C H O I
2 3 2 19 21
(PhCH 2 2 11 17 3
2) NaCl NaHCO 3
CH 2 CH 2 OCH 3
OH
CH
3
(e) Si(CH 3 2 ) Ph (f) CH OC H 1) (+)-(Ipc) BH
2
H C 2 16 33 C H O
C H 2 21 44 3
–
11 23 1) 9-BBN CH OCH 2) OH, H O
OTBDMS C H O Si 2 2 3 2 2
70
2
36
–
H H 2) OH, H O
C H 2 2
6 13
(g) CO 2 H I 2 (h)
2
C C 8 H O I CO H
H 2 13 2 N
CH CN
CH 3 CH 3 1) NBS
3
Ph C H NO
2) NaOCH 16 21
CH 3
3
(i) OTBDMS
1) B H
2 6
H O Si
C 24
O O CH 3 2) OH, H O 44 4
–
2 2
CH CH
3 3
4.13. Some synthetic transformations are shown in the retrosynthetic format. Propose
a short series of reactions (no more than three steps should be necessary) that
could effect each conversion.
(a) O O O O
CH(CH )
3 2
O N O N CH CH(CH )
2
3 2
NH 2
CH Ph CH Ph
2
2
OH
CH 2
(b)
O
CH CH CO CH
(c) I CHCH CH CH CO CH 3 CH 2 2 2 2 3
2
2
2
2
HO
S H
H H
H
CH(CH ) CH 3
2 4
CH(CH ) CH 3
2 4
HO H HO H O 2 CCH 3
OH
(d) O O
O
HN CNH 2
O
Br