TY - JOUR
T1 - 11-Step Total Synthesis of Pallambins C and D
AU - Martinez, Luisruben P.
AU - Umemiya, Shigenobu
AU - Wengryniuk, Sarah E.
AU - Baran, Phil S.
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/6/22
Y1 - 2016/6/22
N2 - The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored.
AB - The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored.
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U2 - 10.1021/jacs.6b04816
DO - 10.1021/jacs.6b04816
M3 - Article
C2 - 27284962
AN - SCOPUS:84975893945
SN - 0002-7863
VL - 138
SP - 7536
EP - 7539
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 24
ER -