CH3 CH3 (d) || TBS OR TBS OR O OR' OR CH3 TBS OR O OH CH3 TBS OR O TBS

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter26: Aldol And Claisen Reactions
Section: Chapter Questions
Problem 26E
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Need help on part D and E only 

1. The total synthesis of Pironetin was accomplished using several steps we have learned this
semester. Some steps are shown below. For each step of the synthesis, identify the functional
group transformation that occurs, and provide reagents that will accomplish this transformation.
Functional Group Transformation
TBS
он OR O ОРМВ
TBS
OTs OR O
ОРМB
(a)
1° Alcohol to Tosylate
TBS
TBS
OR O
OPMB
OTs OR O
ОРМВ
(b)
H
TBS
TBS
(c)
OR O
ОРМB
OR O
OPMB
CH3
CH3
(d)
TBS
TBS
OR O
OR
OR O
OR'
CH3
TBS
CH3
(e)
OR O
TBS
OR O
OH
TBS=
CH3
ОMe Oн О
PMB
OMe
Pironetin
Transcribed Image Text:1. The total synthesis of Pironetin was accomplished using several steps we have learned this semester. Some steps are shown below. For each step of the synthesis, identify the functional group transformation that occurs, and provide reagents that will accomplish this transformation. Functional Group Transformation TBS он OR O ОРМВ TBS OTs OR O ОРМB (a) 1° Alcohol to Tosylate TBS TBS OR O OPMB OTs OR O ОРМВ (b) H TBS TBS (c) OR O ОРМB OR O OPMB CH3 CH3 (d) TBS TBS OR O OR OR O OR' CH3 TBS CH3 (e) OR O TBS OR O OH TBS= CH3 ОMe Oн О PMB OMe Pironetin
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