Synthesis, determination of the absolute stereochemistry, and evaluations at the nicotinic acetylcholine receptors of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

Dejun Zhou; Naoki Toyooka; Hideo Nemoto; Kaoru Yamaguchi; Hiroshi Tsuneki; Tsutomu Wada; Toshiyasu Sasaoka; Hideki Sakai; Yasuhiro Tezuka; Shigetoshi Kadota; Tappey H. Jones; H. Martin Garraffo; Thomas F. Spande; John W. Daly

doi:10.3987/COM-08-S(D)16

Synthesis, determination of the absolute stereochemistry, and evaluations at the nicotinic acetylcholine receptors of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

Dejun Zhou^*, Naoki Toyooka, Hideo Nemoto, Kaoru Yamaguchi, Hiroshi Tsuneki, Tsutomu Wada, Toshiyasu Sasaoka, Hideki Sakai, Yasuhiro Tezuka, Shigetoshi Kadota, Tappey H. Jones, H. Martin Garraffo, Thomas F. Spande, John W. Daly

^*Corresponding author for this work

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

5 Scopus citations

Abstract

The first chiral synthesis of new hydroxyindolizidine alkaloid (1) detected in the ant Myrmicaria melanogaster has been achieved, and its absolute stereochemistry was determined to be 3S, 5R, 8S, 9S by the present chiral synthesis.

Original language	English
Pages (from-to)	565-571
Number of pages	7
Journal	Heterocycles
Volume	79
Issue number	C
DOIs	https://doi.org/10.3987/COM-08-S(D)16
State	Published - 2009

Keywords

Hydroxyindolizidine Alkaloid
Martin's Protocol
Myrmicaria melanogaster
Neuronal Nicotinic Acetylcholine Receptor
α4β2 Nicotinic Receptor

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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Zhou, D., Toyooka, N., Nemoto, H., Yamaguchi, K., Tsuneki, H., Wada, T., Sasaoka, T., Sakai, H., Tezuka, Y., Kadota, S., Jones, T. H., Garraffo, H. M., Spande, T. F., & Daly, J. W. (2009). Synthesis, determination of the absolute stereochemistry, and evaluations at the nicotinic acetylcholine receptors of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster. Heterocycles, 79(C), 565-571. https://doi.org/10.3987/COM-08-S(D)16

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title = "Synthesis, determination of the absolute stereochemistry, and evaluations at the nicotinic acetylcholine receptors of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster",

abstract = "The first chiral synthesis of new hydroxyindolizidine alkaloid (1) detected in the ant Myrmicaria melanogaster has been achieved, and its absolute stereochemistry was determined to be 3S, 5R, 8S, 9S by the present chiral synthesis.",

keywords = "Hydroxyindolizidine Alkaloid, Martin's Protocol, Myrmicaria melanogaster, Neuronal Nicotinic Acetylcholine Receptor, α4β2 Nicotinic Receptor",

author = "Dejun Zhou and Naoki Toyooka and Hideo Nemoto and Kaoru Yamaguchi and Hiroshi Tsuneki and Tsutomu Wada and Toshiyasu Sasaoka and Hideki Sakai and Yasuhiro Tezuka and Shigetoshi Kadota and Jones, {Tappey H.} and Garraffo, {H. Martin} and Spande, {Thomas F.} and Daly, {John W.}",

year = "2009",

doi = "10.3987/COM-08-S(D)16",

language = "英語",

volume = "79",

pages = "565--571",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "C",

}

Zhou, D, Toyooka, N, Nemoto, H, Yamaguchi, K, Tsuneki, H , Wada, T , Sasaoka, T , Sakai, H, Tezuka, Y, Kadota, S, Jones, TH, Garraffo, HM, Spande, TF & Daly, JW 2009, 'Synthesis, determination of the absolute stereochemistry, and evaluations at the nicotinic acetylcholine receptors of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster', Heterocycles, vol. 79, no. C, pp. 565-571. https://doi.org/10.3987/COM-08-S(D)16

TY - JOUR

T1 - Synthesis, determination of the absolute stereochemistry, and evaluations at the nicotinic acetylcholine receptors of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

AU - Zhou, Dejun

AU - Toyooka, Naoki

AU - Nemoto, Hideo

AU - Yamaguchi, Kaoru

AU - Tsuneki, Hiroshi

AU - Wada, Tsutomu

AU - Sasaoka, Toshiyasu

AU - Sakai, Hideki

AU - Tezuka, Yasuhiro

AU - Kadota, Shigetoshi

AU - Jones, Tappey H.

AU - Garraffo, H. Martin

AU - Spande, Thomas F.

AU - Daly, John W.

PY - 2009

Y1 - 2009

N2 - The first chiral synthesis of new hydroxyindolizidine alkaloid (1) detected in the ant Myrmicaria melanogaster has been achieved, and its absolute stereochemistry was determined to be 3S, 5R, 8S, 9S by the present chiral synthesis.

AB - The first chiral synthesis of new hydroxyindolizidine alkaloid (1) detected in the ant Myrmicaria melanogaster has been achieved, and its absolute stereochemistry was determined to be 3S, 5R, 8S, 9S by the present chiral synthesis.

KW - Hydroxyindolizidine Alkaloid

KW - Martin's Protocol

KW - Myrmicaria melanogaster

KW - Neuronal Nicotinic Acetylcholine Receptor

KW - α4β2 Nicotinic Receptor

UR - http://www.scopus.com/inward/record.url?scp=67651092311&partnerID=8YFLogxK

U2 - 10.3987/COM-08-S(D)16

DO - 10.3987/COM-08-S(D)16

M3 - 学術論文

AN - SCOPUS:67651092311

SN - 0385-5414

VL - 79

SP - 565

EP - 571

JO - Heterocycles

JF - Heterocycles

IS - C

ER -

Synthesis, determination of the absolute stereochemistry, and evaluations at the nicotinic acetylcholine receptors of a hydroxyindolizidine alkaloid from the ant Myrmicaria melanogaster

Abstract

Keywords

ASJC Scopus subject areas

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