Scheme 4. Cyclization of Per Hydroxy Ketone 11 vs C(5)- Hydroxy Ketone 10 Method A desired 6-ring cyclization OH OH 4 HO. 5 ОН ОН CI 11 undesired 5-ring cyclization Method B desired 6-ring cyclization CI OH "OH HO "OH OH 12 CI HO OH HO OH OH 13 CI OAC OH OAC O AcO 5 OAC OAC - OH ACO "OAC CI OAC 10 14 12
Scheme 4. Cyclization of Per Hydroxy Ketone 11 vs C(5)- Hydroxy Ketone 10 Method A desired 6-ring cyclization OH OH 4 HO. 5 ОН ОН CI 11 undesired 5-ring cyclization Method B desired 6-ring cyclization CI OH "OH HO "OH OH 12 CI HO OH HO OH OH 13 CI OAC OH OAC O AcO 5 OAC OAC - OH ACO "OAC CI OAC 10 14 12
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:Scheme 4. Cyclization of Per Hydroxy Ketone 11 vs C(5)-
Hydroxy Ketone 10
Method A desired 6-ring cyclization
OH OH
4
HO.
5
ОН ОН
CI
11
undesired 5-ring cyclization
Method B desired 6-ring cyclization
CI
OH
"OH
HO
"OH
OH
12
CI
HO
OH
HO
OH
OH
13
CI
OAC
OH OAC O
AcO
5
OAC OAC
-
OH
ACO
"OAC
CI
OAC
10
14
12
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