Divergent Total Syntheses of Isobatzellines A/B and
Batzelline A
Posted on 2020-07-05 - 20:29
Divergent total syntheses of isobatzellines
A/B and batzelline
A were accomplished. A fully substituted common indole intermediate
bearing C-2 methylthio and C-5 chloro groups was constructed via ring
expansion of benzocyclobutenone oxime sulfonate with NaSMe and a benzyne-mediated
cyclization/functionalization sequence as the key steps. The total
synthesis of isobatzelline B was achieved via formation of the iminoquinone
structure by the redox-neutral acid-promoted C-5 proto-dechlorination
of the common indole intermediate. The total syntheses of isobatzelline
A and batzelline A were completed in a divergent manner by oxidation
of the common indole intermediate using MnO2 or Mn(OAc)3, respectively.
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Yamashita, Yumi; Poignant, Louna; Sakata, Juri; Tokuyama, Hidetoshi (1753). Divergent Total Syntheses of Isobatzellines A/B and
Batzelline A. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.0c01894
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AUTHORS (4)
YY
Yumi Yamashita
LP
Louna Poignant
JS
Juri Sakata
HT
Hidetoshi Tokuyama