Total synthesis of (–)-zephyranthine

Koki Ishii; Yuna Seki-Yoritate; Mizuki Ishibashi; Ming Wai Liaw; Takeshi Oishi; Takaaki Sato; Noritaka Chida

doi:10.3987/COM-18-S(F)40

Total synthesis of (–)-zephyranthine

Koki Ishii, Yuna Seki-Yoritate, Mizuki Ishibashi, Ming Wai Liaw, Takeshi Oishi, Takaaki Sato, Noritaka Chida

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

3 Citations (Scopus)

Abstract

– Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.

Original language	English
Pages (from-to)	111-117
Number of pages	7
Journal	Heterocycles
Volume	99
Issue number	1
DOIs	https://doi.org/10.3987/COM-18-S(F)40
Publication status	Published - 2019

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Total synthesis of (–)-zephyranthine",

abstract = "– Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.",

author = "Koki Ishii and Yuna Seki-Yoritate and Mizuki Ishibashi and Liaw, {Ming Wai} and Takeshi Oishi and Takaaki Sato and Noritaka Chida",

note = "Funding Information: This research was partially supported by a Grant-in-Aid for Scientific Research (B) from MEXT Publisher Copyright: {\textcopyright} 2019 The Japan Institute of Heterocyclic Chemistry",

year = "2019",

doi = "10.3987/COM-18-S(F)40",

language = "English",

volume = "99",

pages = "111--117",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

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TY - JOUR

T1 - Total synthesis of (–)-zephyranthine

AU - Ishii, Koki

AU - Seki-Yoritate, Yuna

AU - Ishibashi, Mizuki

AU - Liaw, Ming Wai

AU - Oishi, Takeshi

AU - Sato, Takaaki

AU - Chida, Noritaka

PY - 2019

Y1 - 2019

N2 - – Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.

AB - – Stereoselective total synthesis of (–)-zephyranthine 1 based on the chiral pool approach starting from D-arabinose is described. The three consecutive chiral centers in (–)-zephyranthine were effectively constructed by the sequential [3,3] sigmatropic rearrangements (Claisen, Overman, and Claisen rearrangements) with chirality transfer of the hydroxy groups in D-arabinose.

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U2 - 10.3987/COM-18-S(F)40

DO - 10.3987/COM-18-S(F)40

M3 - Article

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VL - 99

SP - 111

EP - 117

JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

Total synthesis of (–)-zephyranthine

Abstract

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