Page 639 - Advanced Organic Chemistry Part B - Reactions & Synthesis

(l) O 613
O PROBLEMS
from OH

CH CH 2
(m) HO CH 3
CH 3 O CH 3
from CH 3
CH 3
CH 2
CH 3 H H
CH 2 OTBDPS
(n) CH 3 CO 2
H CH 3 CO 2 CH 2 OTBDPS
H
CH 3
from (CH 2 ) 4 NO 2
H CH 3
HO O
(o) O
CO 2 C 2 H 5
H O O SPh
from and
CH 2 OH CO 2 C 2 H 5 BrCH 2 C C(CH 3 ) 2
CH 2
CH 3
(p) O
CH 3
from and
O
O O
CH 3
(q) CH 3 CH 3
PhCH 2 O PhCH 2 O
CH 3 from CH 3 and
O CH O CH
CH 3
H 2 C (CH 3 ) 2 C CHCH 2 CH 2 Br,
CH 3
(r)
O
C 6 H 13 O
NH from
OH PhO C 6 H 13
NHOH
PhOCH 2
(s) CO 2 C 2 H 5 CO 2 C 2 H 5
O
O O O
from
N N
O O
O O
(t) PhCH 2
CH 3
CH 3 CH 3
OTBDMS from and
CH 3 O 2 C N O CH 3
CH 3
(CH 3 ) 3 CS
O
SC(CH 3 ) 3 O
CH O
6.14. By retrosynthetic analysis, identify a precursor that could provide the desired
product by a single pericyclic reaction. Indicate appropriate reaction conditions
for the transformation you identify.