TY - JOUR
T1 - Stereoselective Syntheses of trans-Anhydromevalonic Acid and trans-Anhydromevalonyl Group-Containing Natural Products
AU - Nakayama, Atsushi
AU - Yasuno, Yoko
AU - Yamamoto, Yuki
AU - Saito, Kai
AU - Kitsuwa, Kohei
AU - Okamura, Hironori
AU - Shinada, Tetsuro
N1 - Funding Information:
This work was financially supported by JSPS KAKENHI (JP19H04661, JP19H04651, JP20K09396, and JP21K14629), the OCU ‘Think globally, act locally’ Research Grant for Young Scientists 2021 through the hometown donation fund of Osaka City, the Uehara Memorial Foundation, and the Sasakawa Scientific Research Grant from The Japan Science Society.
Publisher Copyright:
©
PY - 2021
Y1 - 2021
N2 - Collective total syntheses of trans-anhydromevalonic acid (tAHMA) and trans-anhydromevalonyl (tAHM) group-containing natural products (pestalotiopin A, pestalotiopamide C, pestalotiopamide D, farinomalein E, eleutherazine B, and trichocyclodipeptide A) were achieved using tAHMA esters as key intermediates. To this end, tAHMA tert-butyl ester was newly prepared by Z-vinyltosylation of tert-butyl 3-oxo-5-((triisopropylsilyl)oxy)pentanoate followed by the Negishi cross-coupling reaction with Me2Zn. tAHMA esters were converted to the target natural products via esterification or amidation. Comparison of the spectroscopic data of synthetic and natural products confirmed the E-configuration of the tAHM moieties in the natural products.
AB - Collective total syntheses of trans-anhydromevalonic acid (tAHMA) and trans-anhydromevalonyl (tAHM) group-containing natural products (pestalotiopin A, pestalotiopamide C, pestalotiopamide D, farinomalein E, eleutherazine B, and trichocyclodipeptide A) were achieved using tAHMA esters as key intermediates. To this end, tAHMA tert-butyl ester was newly prepared by Z-vinyltosylation of tert-butyl 3-oxo-5-((triisopropylsilyl)oxy)pentanoate followed by the Negishi cross-coupling reaction with Me2Zn. tAHMA esters were converted to the target natural products via esterification or amidation. Comparison of the spectroscopic data of synthetic and natural products confirmed the E-configuration of the tAHM moieties in the natural products.
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U2 - 10.1021/acs.jnatprod.1c01176
DO - 10.1021/acs.jnatprod.1c01176
M3 - Article
C2 - 35195424
AN - SCOPUS:85125877944
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
ER -