In:
Angewandte Chemie, Wiley, Vol. 128, No. 9 ( 2016-02-24), p. 3164-3168
Abstract:
Reported is the first scalable synthesis of rac ‐jungermannenones B and C starting from the commercially available and inexpensive geraniol in 10 and 9 steps, respectively. The unique jungermannenone framework is rapidly assembled by an unprecedented regioselective 1,6‐dienyne reductive cyclization reaction which proceeds through a vinyl radical cyclization/allylic radical isomerization mechanism. DFT calculations explain the high regioselectivity observed in the 1,6‐dienyne reductive radical cyclization.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.201511659
Language:
English
Publisher:
Wiley
Publication Date:
2016
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