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

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

8 Scopus citations

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.

Original language	English
Article number	7529
Journal	Molecules
Volume	26
Issue number	24
DOIs	https://doi.org/10.3390/molecules26247529
State	Published - Dec 1 2021

Bibliographical note

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/).

Keywords

Cis-195A
Cis-211A
Decahydroquinoline
Poison frog alkaloid

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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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), Article 7529. https://doi.org/10.3390/molecules26247529

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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/).",

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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 - https://www.scopus.com/pages/publications/85121563234

UR - https://www.scopus.com/pages/publications/85121563234#tab=citedBy

U2 - 10.3390/molecules26247529

DO - 10.3390/molecules26247529

M3 - Article

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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