TY - JOUR
T1 - Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols
T2 - Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives
AU - Sherwood, Alexander M.
AU - Williamson, Samuel E.
AU - Johnson, Stephanie N.
AU - Yilmaz, Anil
AU - Day, Victor W.
AU - Prisinzano, Thomas E.
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2018/1/19
Y1 - 2018/1/19
N2 - A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.
AB - A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.
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U2 - 10.1021/acs.joc.7b02324
DO - 10.1021/acs.joc.7b02324
M3 - Article
C2 - 29271194
AN - SCOPUS:85040829838
SN - 0022-3263
VL - 83
SP - 980
EP - 992
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -