Efficient Synthesis of (-)-Hanishin, (-)-Longamide B, and (-)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

Zenyu Shiokawa; Shinsuke Inuki; Koichi Fukase; Yukari Fujimoto

doi:10.1055/s-0035-1560988

Efficient Synthesis of (-)-Hanishin, (-)-Longamide B, and (-)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

Zenyu Shiokawa, Shinsuke Inuki, Koichi Fukase, Yukari Fujimoto

Department of Chemistry

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

8 Citations (Scopus)

Abstract

We describe a simple chiral-pool synthesis of (-)-longamide B, (-)-longamide B methyl ester, and (-)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolopiperazinone core scaffold.

Original language	English
Article number	st-2015-u0727-l
Pages (from-to)	616-620
Number of pages	5
Journal	Synlett
Volume	27
Issue number	4
DOIs	https://doi.org/10.1055/s-0035-1560988
Publication status	Published - 2016 Mar 1

Keywords

asymmetric synthesis
hanishin
heterocycles
longamide B
piperazinones
sulfamidates

ASJC Scopus subject areas

Organic Chemistry

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title = "Efficient Synthesis of (-)-Hanishin, (-)-Longamide B, and (-)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates",

abstract = "We describe a simple chiral-pool synthesis of (-)-longamide B, (-)-longamide B methyl ester, and (-)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolopiperazinone core scaffold.",

keywords = "asymmetric synthesis, hanishin, heterocycles, longamide B, piperazinones, sulfamidates",

author = "Zenyu Shiokawa and Shinsuke Inuki and Koichi Fukase and Yukari Fujimoto",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart, New York 2016.",

year = "2016",

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doi = "10.1055/s-0035-1560988",

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T1 - Efficient Synthesis of (-)-Hanishin, (-)-Longamide B, and (-)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

AU - Shiokawa, Zenyu

AU - Inuki, Shinsuke

AU - Fukase, Koichi

AU - Fujimoto, Yukari

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart, New York 2016.

PY - 2016/3/1

Y1 - 2016/3/1

N2 - We describe a simple chiral-pool synthesis of (-)-longamide B, (-)-longamide B methyl ester, and (-)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolopiperazinone core scaffold.

AB - We describe a simple chiral-pool synthesis of (-)-longamide B, (-)-longamide B methyl ester, and (-)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolopiperazinone core scaffold.

KW - asymmetric synthesis

KW - hanishin

KW - heterocycles

KW - longamide B

KW - piperazinones

KW - sulfamidates

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SP - 616

EP - 620

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 4

M1 - st-2015-u0727-l

ER -

Efficient Synthesis of (-)-Hanishin, (-)-Longamide B, and (-)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

Abstract

Keywords

ASJC Scopus subject areas

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