TY - JOUR
T1 - Stepwise approach for sterically hindered Csp3-Csp3 bond formation by dehydrogenative
T2 - O -alkylation and Lewis acid-catalyzed [1,3]-rearrangement towards the arylalkylcyclopentane skeleton of sesquiterpenes
AU - Fujitani, Ban
AU - Hanaya, Kengo
AU - Sugai, Takeshi
AU - Higashibayashi, Shuhei
N1 - Publisher Copyright:
This journal is © The Royal Society of Chemistry.
PY - 2020/3/28
Y1 - 2020/3/28
N2 - A stepwise dehydrogenative cross-coupling method was developed for the formation of sterically hindered Csp3-Csp3 bonds. Intramolecular dehydrogenative O-alkylation of a β-ketoester by 2,3-dichloro-5,6-dicyano-p-benzoquinone to form an oxolane followed by Lewis acid-catalyzed [1,3]-rearrangement furnished the sesquiterpene arylmethylcyclopentane skeleton. The formal syntheses of herbertane-type β-herbertenol, cuparane-type enokipodins A and B were also achieved.
AB - A stepwise dehydrogenative cross-coupling method was developed for the formation of sterically hindered Csp3-Csp3 bonds. Intramolecular dehydrogenative O-alkylation of a β-ketoester by 2,3-dichloro-5,6-dicyano-p-benzoquinone to form an oxolane followed by Lewis acid-catalyzed [1,3]-rearrangement furnished the sesquiterpene arylmethylcyclopentane skeleton. The formal syntheses of herbertane-type β-herbertenol, cuparane-type enokipodins A and B were also achieved.
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U2 - 10.1039/d0cc01017k
DO - 10.1039/d0cc01017k
M3 - Article
C2 - 32104846
AN - SCOPUS:85082542314
SN - 1359-7345
VL - 56
SP - 3621
EP - 3624
JO - Chemical Communications
JF - Chemical Communications
IS - 25
ER -