Asymmetric Synthesis of the Aromatic Fragment of Sespendole

Yoshiki Ono; Atsuo Nakazaki; Kaori Ueki; Keiko Higuchi; Uraiwan Sriphana; Masaatsu Adachi; Toshio Nishikawa

doi:10.1021/acs.joc.9b01597

Asymmetric Synthesis of the Aromatic Fragment of Sespendole

Yoshiki Ono, Atsuo Nakazaki, Kaori Ueki, Keiko Higuchi, Uraiwan Sriphana, Masaatsu Adachi, Toshio Nishikawa

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Sespendole is an indole sesquiterpene alkaloid bearing two isoprenyl groups, one of which is highly oxidized. Herein, we disclose an eight-step synthesis of the aromatic fragment of sespendole in an optically pure form, starting from 4-bromo-2-fluoronitrobenzene. The key steps were a Claisen rearrangement at room temperature for introduction of the prenyl group and a coupling between the dianion generated from prenylated bromo-N-tosylanilide and a chiral epoxy aldehyde. ©

Original language	English
Pages (from-to)	9750-9757
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	84
Issue number	15
DOIs	https://doi.org/10.1021/acs.joc.9b01597
Publication status	Published - 2019 Aug 2
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Asymmetric Synthesis of the Aromatic Fragment of Sespendole",

abstract = "Sespendole is an indole sesquiterpene alkaloid bearing two isoprenyl groups, one of which is highly oxidized. Herein, we disclose an eight-step synthesis of the aromatic fragment of sespendole in an optically pure form, starting from 4-bromo-2-fluoronitrobenzene. The key steps were a Claisen rearrangement at room temperature for introduction of the prenyl group and a coupling between the dianion generated from prenylated bromo-N-tosylanilide and a chiral epoxy aldehyde. {\textcopyright}",

author = "Yoshiki Ono and Atsuo Nakazaki and Kaori Ueki and Keiko Higuchi and Uraiwan Sriphana and Masaatsu Adachi and Toshio Nishikawa",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (B) (No. 16H04915), Grants-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Frontier Research on Chemical Communication{\textquoteright}{\textquoteright} (No. 17H06406), and “Middle Molecular Strategy” (No.18H04400) from MEXT. Y.O. would like to thank the Program for Leading Graduate Schools: IGER Program in Green Natural Sciences from MEXT and the Mizutani Scholarship (Graduate School of Bioagricultural Sciences, Nagoya University). K.H. was a research fellow of the Japan Society for the Promotion of Science (DC1). U.S. would like to thank the Golden Jubilee PhD program (Thailand). We would also like to thank Dr. H. Yamada and Dr. S. Ueno for helpful discussion and technical assistance. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.joc.9b01597",

language = "English",

volume = "84",

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T1 - Asymmetric Synthesis of the Aromatic Fragment of Sespendole

AU - Ono, Yoshiki

AU - Nakazaki, Atsuo

AU - Ueki, Kaori

AU - Higuchi, Keiko

AU - Sriphana, Uraiwan

AU - Adachi, Masaatsu

AU - Nishikawa, Toshio

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (B) (No. 16H04915), Grants-in-Aid for Scientific Research on Innovative Areas ‘Frontier Research on Chemical Communication’’ (No. 17H06406), and “Middle Molecular Strategy” (No.18H04400) from MEXT. Y.O. would like to thank the Program for Leading Graduate Schools: IGER Program in Green Natural Sciences from MEXT and the Mizutani Scholarship (Graduate School of Bioagricultural Sciences, Nagoya University). K.H. was a research fellow of the Japan Society for the Promotion of Science (DC1). U.S. would like to thank the Golden Jubilee PhD program (Thailand). We would also like to thank Dr. H. Yamada and Dr. S. Ueno for helpful discussion and technical assistance. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/8/2

Y1 - 2019/8/2

N2 - Sespendole is an indole sesquiterpene alkaloid bearing two isoprenyl groups, one of which is highly oxidized. Herein, we disclose an eight-step synthesis of the aromatic fragment of sespendole in an optically pure form, starting from 4-bromo-2-fluoronitrobenzene. The key steps were a Claisen rearrangement at room temperature for introduction of the prenyl group and a coupling between the dianion generated from prenylated bromo-N-tosylanilide and a chiral epoxy aldehyde. ©

AB - Sespendole is an indole sesquiterpene alkaloid bearing two isoprenyl groups, one of which is highly oxidized. Herein, we disclose an eight-step synthesis of the aromatic fragment of sespendole in an optically pure form, starting from 4-bromo-2-fluoronitrobenzene. The key steps were a Claisen rearrangement at room temperature for introduction of the prenyl group and a coupling between the dianion generated from prenylated bromo-N-tosylanilide and a chiral epoxy aldehyde. ©

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JF - Journal of Organic Chemistry

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Asymmetric Synthesis of the Aromatic Fragment of Sespendole

Abstract

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