Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol

Kenichi Takao, Sakamoto Shu, Marianne Ayaka Touati, Yusuke Kusakawa, Kin Ichi Tadano

Research output: Contribution to journal › Article

11 Citations (Scopus)

Abstract

An asymmetric Claisen rearrangement using Oppolzer's camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.

Original languageEnglish
Pages (from-to)13330-13344
Number of pages15
JournalMolecules
Volume17
Issue number11
DOIs
Publication statusPublished - 2012 Nov

Fingerprint

Stereoselectivity
Carbon
Hot Temperature
carbon
Substrates
synthesis
products
configurations
bakuchiol
camphorsultam
geraniol

Keywords

  • Camphorsultam
  • Chiral auxiliary
  • Claisen rearrangement
  • Quaternary stereocenter
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol. / Takao, Kenichi; Shu, Sakamoto; Touati, Marianne Ayaka; Kusakawa, Yusuke; Tadano, Kin Ichi.

In: Molecules, Vol. 17, No. 11, 11.2012, p. 13330-13344.

Research output: Contribution to journal › Article

Takao, K, Shu, S, Touati, MA, Kusakawa, Y & Tadano, KI 2012, 'Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol', Molecules, vol. 17, no. 11, pp. 13330-13344. https://doi.org/10.3390/molecules171113330
Takao K, Shu S, Touati MA, Kusakawa Y, Tadano KI. Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol. Molecules. 2012 Nov;17(11):13330-13344. https://doi.org/10.3390/molecules171113330
Takao, Kenichi ; Shu, Sakamoto ; Touati, Marianne Ayaka ; Kusakawa, Yusuke ; Tadano, Kin Ichi. / Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated claisen rearrangement and total synthesis of (+)-Bakuchiol. In: Molecules. 2012 ; Vol. 17, No. 11. pp. 13330-13344.
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