First enantioselective synthesis of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

Naoki Toyooka; Dejun Zhou; Hideo Nemoto; Yasuhiro Tezuka; Shigetoshi Kadota; Tappey H. Jones; H. Martin Garraffo; Thomas F. Spande; John W. Daly

doi:10.1055/s-2008-1078502

First enantioselective synthesis of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

Naoki Toyooka^*, Dejun Zhou, Hideo Nemoto, Yasuhiro Tezuka, Shigetoshi Kadota, Tappey H. Jones, H. Martin Garraffo, Thomas F. Spande, John W. Daly

^*Corresponding author for this work

Life Sciences and Bioengineering

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

16 Scopus citations

Abstract

The first enantioselective synthesis of the recently reported ant alkaloid 1 has been achieved starting from commercially available lactam 3 in seven steps and 25% overall yield. The proposed structure of the natural product was confirmed by comparison with synthetic 1 and its absolute configuration established as 3S,5R,8S,9S.

Original language	English
Pages (from-to)	1894-1896
Number of pages	3
Journal	Synlett
Issue number	12
DOIs	https://doi.org/10.1055/s-2008-1078502
State	Published - 2008/07/16

Keywords

Chelation control
Hydroxyindolizidine
Myrmicaria melanogaster
New ant alkaloid
Venoms of ant

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-2008-1078502

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title = "First enantioselective synthesis of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster",

abstract = "The first enantioselective synthesis of the recently reported ant alkaloid 1 has been achieved starting from commercially available lactam 3 in seven steps and 25% overall yield. The proposed structure of the natural product was confirmed by comparison with synthetic 1 and its absolute configuration established as 3S,5R,8S,9S.",

keywords = "Chelation control, Hydroxyindolizidine, Myrmicaria melanogaster, New ant alkaloid, Venoms of ant",

author = "Naoki Toyooka and Dejun Zhou and Hideo Nemoto and Yasuhiro Tezuka and Shigetoshi Kadota and Jones, {Tappey H.} and Garraffo, {H. Martin} and Spande, {Thomas F.} and Daly, {John W.}",

year = "2008",

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doi = "10.1055/s-2008-1078502",

language = "英語",

pages = "1894--1896",

journal = "Synlett",

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publisher = "Georg Thieme Verlag",

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T1 - First enantioselective synthesis of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

AU - Toyooka, Naoki

AU - Zhou, Dejun

AU - Nemoto, Hideo

AU - Tezuka, Yasuhiro

AU - Kadota, Shigetoshi

AU - Jones, Tappey H.

AU - Garraffo, H. Martin

AU - Spande, Thomas F.

AU - Daly, John W.

PY - 2008/7/16

Y1 - 2008/7/16

N2 - The first enantioselective synthesis of the recently reported ant alkaloid 1 has been achieved starting from commercially available lactam 3 in seven steps and 25% overall yield. The proposed structure of the natural product was confirmed by comparison with synthetic 1 and its absolute configuration established as 3S,5R,8S,9S.

AB - The first enantioselective synthesis of the recently reported ant alkaloid 1 has been achieved starting from commercially available lactam 3 in seven steps and 25% overall yield. The proposed structure of the natural product was confirmed by comparison with synthetic 1 and its absolute configuration established as 3S,5R,8S,9S.

KW - Chelation control

KW - Hydroxyindolizidine

KW - Myrmicaria melanogaster

KW - New ant alkaloid

KW - Venoms of ant

UR - http://www.scopus.com/inward/record.url?scp=48349096838&partnerID=8YFLogxK

U2 - 10.1055/s-2008-1078502

DO - 10.1055/s-2008-1078502

M3 - 学術論文

AN - SCOPUS:48349096838

SN - 0936-5214

SP - 1894

EP - 1896

JO - Synlett

JF - Synlett

IS - 12

ER -

First enantioselective synthesis of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

Abstract

Keywords

ASJC Scopus subject areas

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