Page 230 - Advanced Organic Chemistry Part B - Reactions & Synthesis

202 H CH 3
O CH 2
H (h) H C C
C 12 25
(g) O O TBDPSO 2
CHAPTER 2 CH CH CCH
2 2 3 O
Reactions of Carbon O
Nucleophiles with (i) (j) O O O O O
Carbonyl Compounds
H 5 C 2 O 2 CCH 2 CH 2 CO 2 C 2 H 5
Ph CCH 2 CCH Ph CCH CCH C
3 2 2 OCH 3
(k) O (l)
O O O
CH O CCH CH O CCH CH CH O CH CH O CH CHCH CH
3 3 3 2 3 3 2
(m) CH 3 O CH O
3
C CHSCH CH CH CH
H 3 2 2 2 3
CH 3
(n) CH 3
O O O CH
CH CH
3
3
N CSCH 2 CH 3 N CSCH 2 CH 3
H H
O O
CH (p)
(o) CH 3 3 CH 3 CH 3
CH 3 CH 3 (CH ) CH (CH ) CH
3 2
3 2
CH 3 CH 3 O O CHOCH
O 3
O CH 2
(q) H H
(r) H CH O
(CH ) CCC(CH ) (CH 3 3 ) CCC(CH ) H H
3 3 3 3 3 3
Ph Ph
Ph Ph H Ph
(s) H CO 2 CH 3 (t)
(CH ) CHCH O H
3 2
H O
O
(CH ) CH H Ph
3 2
(u) (v)
(CH 3 3 ) SiO O
O Ph
PhCH C(CO CH )
2 3 2
CH )
(CH ) CS CH(CO 2 3 2
3 3
CH 3
(w) (x)
CH CH (CH ) CH CO 2 H
3 H 3 (CH ) CHCH CO H 3 2
3 2
2
2
CH O C
H CO CH 3 2 CH CO C(CH ) CH 2 CH CN
2 3 2 2 3 3 2
CH
3
2.3. Step-by-step retrosynthetic analysis of each of the target molecules reveals that
they can be efficiently prepared in a few steps from the starting material shown
on the right. Do a retrosynthetic analysis and suggest reagents and reaction
conditions for carrying out the desired synthesis.
(a) CH 3
CH 3 (b) O CH(CH 3 ) 2 OH
O O
CCH 3
O
O O
CH(CH 3 ) 2
(d) C 6 H 5
CH(CH 3 ) 2
(c) C 6 H 5 CH CHCH
CCH (CH 3 ) 2 CHCH 2 CH O
CH 2 CHCHCH 2 CH 2 CO 2 CH 2 CH 3
O
CH 3 CH(CH 3 ) 2
(f)
(e) CH 3
CH 3
CH 3 O
OCH 3
CCH 2 CH 2 C CH 3
CH 2
CCH 3
O O O
CH 3
O