NH2 CH;0 CH;O [1]A, benzene HN O. several steps CH;O [2] NaBHa, CH,Oн осн CH;O. н 'o осн OCH, CH30 оCнs CH,Ó ÖCH, reserpine осн, CH;0

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter7: Cycloalkanes
Section: Chapter Questions
Problem 1E
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Draw a stepwise mechanism for the following reactions, two steps in R. B. Woodward’s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwolfia serpentina Benth, was used at one time to manage mild hypertension associated with anxiety.

NH2
CH;0
CH;O
[1]A, benzene
HN
O.
several
steps
CH;O
[2] NaBHa, CH,Oн
осн
CH;O.
н
'o
осн
OCH,
CH30
оCнs
CH,Ó
ÖCH,
reserpine
осн,
CH;0
Transcribed Image Text:NH2 CH;0 CH;O [1]A, benzene HN O. several steps CH;O [2] NaBHa, CH,Oн осн CH;O. н 'o осн OCH, CH30 оCнs CH,Ó ÖCH, reserpine осн, CH;0
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