Total synthesis of decahydroquinoline poison frog alkaloids ent-cis-195a and cis-211a

Takuya Okada; Naizhen Wu; Katsuki Takashima; Jungoh Ishimura; Hiroyuki Morita; Takuya Ito; Takeshi Kodama; Yuhei Yamasaki; Shin Ichi Akanuma; Yoshiyuki Kubo; Ken Ichi Hosoya; Hiroshi Tsuneki; Tsutomu Wada; Toshiyasu Sasaoka; Takahiro Shimizu; Hideki Sakai; Linda P. Dwoskin; Syed R. Hussaini; Ralph A. Saporito; Naoki Toyooka

doi:10.3390/molecules26247529

Total synthesis of decahydroquinoline poison frog alkaloids ent-cis-195a and cis-211a

Takuya Okada^*, Naizhen Wu, Katsuki Takashima, Jungoh Ishimura, Hiroyuki Morita, Takuya Ito, Takeshi Kodama, Yuhei Yamasaki, Shin Ichi Akanuma, Yoshiyuki Kubo, Ken Ichi Hosoya, Hiroshi Tsuneki, Tsutomu Wada, Toshiyasu Sasaoka, Takahiro Shimizu, Hideki Sakai, Linda P. Dwoskin, Syed R. Hussaini, Ralph A. Saporito, Naoki Toyooka^*

^*この論文の責任著者

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

5 被引用数 (Scopus)

抄録

The total synthesis of two decahydroquinoline poison frog alkaloids ent-cis-195A and cis-211A were achieved in 16 steps (38% overall yield) and 19 steps (31% overall yield), respectively, starting from known compound 1. Both alkaloids were synthesized from the common key intermediate 11 in a divergent fashion, and the absolute stereochemistry of natural cis-211A was determined to be 2R, 4aR, 5R, 6S, and 8aS. Interestingly, the absolute configuration of the parent decahydroquinoline nuclei of cis-211A was the mirror image of that of cis-195A, although both alkaloids were isolated from the same poison frog species, Oophaga (Dendrobates) pumilio, from Panama.

本文言語	英語
論文番号	7529
ジャーナル	Molecules
巻	26
号	24
DOI	https://doi.org/10.3390/molecules26247529
出版ステータス	出版済み - 2021/12/01

ASJC Scopus 主題領域

分析化学
化学（その他）
分子医療
薬科学
創薬
物理化学および理論化学
有機化学

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10.3390/molecules26247529

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Okada, T., Wu, N., Takashima, K., Ishimura, J., Morita, H., Ito, T., Kodama, T., Yamasaki, Y., Akanuma, S. I., Kubo, Y., Hosoya, K. I., Tsuneki, H., Wada, T., Sasaoka, T., Shimizu, T., Sakai, H., Dwoskin, L. P., Hussaini, S. R., Saporito, R. A., & Toyooka, N. (2021). Total synthesis of decahydroquinoline poison frog alkaloids ent-cis-195a and cis-211a. Molecules, 26(24), 記事 7529. https://doi.org/10.3390/molecules26247529

@article{a8ecaeb763e84001b96fae301e415c3c,

title = "Total synthesis of decahydroquinoline poison frog alkaloids ent-cis-195a and cis-211a",

abstract = "The total synthesis of two decahydroquinoline poison frog alkaloids ent-cis-195A and cis-211A were achieved in 16 steps (38% overall yield) and 19 steps (31% overall yield), respectively, starting from known compound 1. Both alkaloids were synthesized from the common key intermediate 11 in a divergent fashion, and the absolute stereochemistry of natural cis-211A was determined to be 2R, 4aR, 5R, 6S, and 8aS. Interestingly, the absolute configuration of the parent decahydroquinoline nuclei of cis-211A was the mirror image of that of cis-195A, although both alkaloids were isolated from the same poison frog species, Oophaga (Dendrobates) pumilio, from Panama.",

keywords = "Cis-195A, Cis-211A, Decahydroquinoline, Poison frog alkaloid",

author = "Takuya Okada and Naizhen Wu and Katsuki Takashima and Jungoh Ishimura and Hiroyuki Morita and Takuya Ito and Takeshi Kodama and Yuhei Yamasaki and Akanuma, {Shin Ichi} and Yoshiyuki Kubo and Hosoya, {Ken Ichi} and Hiroshi Tsuneki and Tsutomu Wada and Toshiyasu Sasaoka and Takahiro Shimizu and Hideki Sakai and Dwoskin, {Linda P.} and Hussaini, {Syed R.} and Saporito, {Ralph A.} and Naoki Toyooka",

note = "Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).",

year = "2021",

month = dec,

day = "1",

doi = "10.3390/molecules26247529",

language = "英語",

volume = "26",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "24",

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Okada, T, Wu, N, Takashima, K, Ishimura, J, Morita, H, Ito, T, Kodama, T, Yamasaki, Y, Akanuma, SI, Kubo, Y, Hosoya, KI , Tsuneki, H , Wada, T , Sasaoka, T , Shimizu, T , Sakai, H, Dwoskin, LP, Hussaini, SR, Saporito, RA & Toyooka, N 2021, 'Total synthesis of decahydroquinoline poison frog alkaloids ent-cis-195a and cis-211a', Molecules, vol. 26, no. 24, 7529. https://doi.org/10.3390/molecules26247529

TY - JOUR

T1 - Total synthesis of decahydroquinoline poison frog alkaloids ent-cis-195a and cis-211a

AU - Okada, Takuya

AU - Wu, Naizhen

AU - Takashima, Katsuki

AU - Ishimura, Jungoh

AU - Morita, Hiroyuki

AU - Ito, Takuya

AU - Kodama, Takeshi

AU - Yamasaki, Yuhei

AU - Akanuma, Shin Ichi

AU - Kubo, Yoshiyuki

AU - Hosoya, Ken Ichi

AU - Tsuneki, Hiroshi

AU - Wada, Tsutomu

AU - Sasaoka, Toshiyasu

AU - Shimizu, Takahiro

AU - Sakai, Hideki

AU - Dwoskin, Linda P.

AU - Hussaini, Syed R.

AU - Saporito, Ralph A.

AU - Toyooka, Naoki

N1 - Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).

PY - 2021/12/1

Y1 - 2021/12/1

N2 - The total synthesis of two decahydroquinoline poison frog alkaloids ent-cis-195A and cis-211A were achieved in 16 steps (38% overall yield) and 19 steps (31% overall yield), respectively, starting from known compound 1. Both alkaloids were synthesized from the common key intermediate 11 in a divergent fashion, and the absolute stereochemistry of natural cis-211A was determined to be 2R, 4aR, 5R, 6S, and 8aS. Interestingly, the absolute configuration of the parent decahydroquinoline nuclei of cis-211A was the mirror image of that of cis-195A, although both alkaloids were isolated from the same poison frog species, Oophaga (Dendrobates) pumilio, from Panama.

AB - The total synthesis of two decahydroquinoline poison frog alkaloids ent-cis-195A and cis-211A were achieved in 16 steps (38% overall yield) and 19 steps (31% overall yield), respectively, starting from known compound 1. Both alkaloids were synthesized from the common key intermediate 11 in a divergent fashion, and the absolute stereochemistry of natural cis-211A was determined to be 2R, 4aR, 5R, 6S, and 8aS. Interestingly, the absolute configuration of the parent decahydroquinoline nuclei of cis-211A was the mirror image of that of cis-195A, although both alkaloids were isolated from the same poison frog species, Oophaga (Dendrobates) pumilio, from Panama.

KW - Cis-195A

KW - Cis-211A

KW - Decahydroquinoline

KW - Poison frog alkaloid

UR - http://www.scopus.com/inward/record.url?scp=85121563234&partnerID=8YFLogxK

U2 - 10.3390/molecules26247529

DO - 10.3390/molecules26247529

M3 - 学術論文

C2 - 34946611

AN - SCOPUS:85121563234

SN - 1420-3049

VL - 26

JO - Molecules

JF - Molecules

IS - 24

M1 - 7529

ER -

Total synthesis of decahydroquinoline poison frog alkaloids ent-cis-195a and cis-211a

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