Synthesis via vinyl sulfones. 21. Total synthesis of dl-morphine
β Scribed by Toth, J. E.; Fuchs, P. L.
- Book ID
- 126892905
- Publisher
- American Chemical Society
- Year
- 1987
- Tongue
- English
- Weight
- 338 KB
- Volume
- 52
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
## Abstract __dl__βPumiliotoxinβC **(4)** was synthesized in a practical manner from __trans__β4βhexenal **(9)**. The key step **14** β **15** (__Scheme 3__) involves an intramolecular __Diels__β__Alder__ reaction giving mainly the __cis__βfused indanols **15a**, which were converted to the __cis__
Radical attack on the double bond of 2,3-bis(phenylsulfonyl)-1 -propene leads to an intermediate sulfonyl stabilized radical. This species readily fragments to produce a new vinyl sulfone which can undergo further radical cyclization to give a six ring sulfone.