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 Rauwola 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
Expert Solution
Step 1

Reserpine is used as a drug for the treatment of high pressure usually in the combination of vasodilator. The antihypertensive actions of reserpine are largely due to its antinoradrenergic effects which are a results of its ability to deplete among the neurotransmitter from peripheral sympathetic nerve endings.  

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