TY - JOUR
T1 - A Highly Convergent and Biomimetic Total Synthesis of Portentol
AU - Cheng, Bichu
AU - Trauner, Dirk
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/11/4
Y1 - 2015/11/4
N2 - An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti-anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, then afforded portentol and its known dehydration product, anhydroportentol. The biosynthesis of portentol and the biosynthetic relevance of our key step are discussed.
AB - An efficient total synthesis of the unusual polyketide portentol is reported. Three boron aldol reactions were used to assemble the linear carbon chain of the natural product, which contains two challenging anti-anti stereotriads. A biomimetic double cyclization cascade, triggered by an oxidation, then afforded portentol and its known dehydration product, anhydroportentol. The biosynthesis of portentol and the biosynthetic relevance of our key step are discussed.
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U2 - 10.1021/jacs.5b10009
DO - 10.1021/jacs.5b10009
M3 - Article
C2 - 26471956
AN - SCOPUS:84953391638
SN - 0002-7863
VL - 137
SP - 13800
EP - 13803
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 43
ER -