scholarly journals Total Synthesis of Decahydroquinoline Poison Frog Alkaloids ent-cis-195A and cis-211A

Molecules ◽  
2021 ◽  
Vol 26 (24) ◽  
pp. 7529
Author(s):  
Takuya Okada ◽  
Naizhen Wu ◽  
Katsuki Takashima ◽  
Jungoh Ishimura ◽  
Hiroyuki Morita ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Mirror Image ◽  
Poison Frog ◽  
Dendrobates Pumilio ◽  
Frog Species ◽  
The Common ◽  
The Absolute ◽  
Absolute Stereochemistry

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.

Absolute Stereochemistry of (-)-Wieland-Miescher Ketone as Established by the X-ray Crystallographic and CD Exciton Chirality Methods

1992 ◽  
Vol 57 (7) ◽  
pp. 1459-1465 ◽  
Author(s):  
Nobuyuki Harada ◽  
Tatsuo Sugioka ◽  
Hisashi Uda ◽  
Takeo Kuriki
Keyword(s):  
Structure Analysis ◽  
Absolute Configuration ◽  
X Ray ◽  
The Absolute ◽  
Absolute Stereochemistry

The 8aR absolute stereochemistry of Wieland-Miescher ketone (-)-I was established by the X-ray structure analysis of its bis(4-bromobenzoate) derivatives (1R,6R,8aR)-(+)-IV and (1R,6S,8aR)-(-)-V. The absolute configuration of (-)-I was corroborated further by the application of the CD exciton chirality method to bis(4-bromobenzoates) (+)-IV and (-)-V.

Asymmetric Total Synthesis and Determination of the Absolute Configuration of (+)-Srilankenyne via Sequence-Sensitive Halogenations Guided by Conformational Analysis

2021 ◽  
Vol 23 (4) ◽  
pp. 1321-1326
Author(s):  
Hongjun Jang ◽  
Soo Yeon Kwak ◽  
Dongjoo Lee ◽  
Juan V. Alegre-Requena ◽  
Hyoungsu Kim ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Conformational Analysis ◽  
Absolute Configuration ◽  
Asymmetric Total Synthesis ◽  
The Absolute

Total synthesis and determination of the absolute configuration of (−)-longilene peroxide

2001 ◽  
Vol 42 (36) ◽  
pp. 6307-6309 ◽  
Author(s):  
Yoshiki Morimoto ◽  
Toshiyuki Iwai ◽  
Takamasa Kinoshita
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
The Absolute

(-)-Strempeliopine, stereoselective total synthesis and the determination of absolute configuration

1986 ◽  
Vol 51 (8) ◽  
pp. 1731-1742 ◽  
Author(s):  
Josef Hájíček ◽  
Jan Trojánek
Keyword(s):  
Circular Dichroism ◽  
Total Synthesis ◽  
Absolute Configuration ◽  
Determination Of Absolute Configuration ◽  
Natural Base ◽  
The Absolute ◽  
Circular Dichroïsm

A synthesis of (±)-strempeliopine (II) is described, the key step of which is the stereoselective reductive rearrangement of 18-methylene-1,2-dehydroaspidospermidine (XI). The absolute configuration of the natural (-)-base II was determined as (2S, 7R, 20R, 21R) on the basis of its synthesis from (+)-18-methylenevincadifformine (XVII) the configuration of which was derived from a comparison of circular dichroism properties of bases with a β-anilinoacrylate chromophore. The biogenesis of the alkaloids of the schizozygane type is discussed.

First Total Synthesis and Determination of the Absolute Configuration of Strictifolione, a New 6-(ω-Phenylalkenyl)-5,6-dihydro-α-pyrone, Isolated from Cryptocarya strictifolia.

ChemInform ◽  
2003 ◽  
Vol 34 (7) ◽  
Author(s):  
Lia Dewi Juliawaty ◽  
Yoshimi Watanabe ◽  
Mariko Kitajima ◽  
Sjamsul Arifin Achmad ◽  
Hiromitsu Takayama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
The Absolute

ChemInform Abstract: Total Synthesis and Determination of the Absolute Configuration of FD-838, a Naturally Occurring Azaspirobicyclic Product.

ChemInform ◽  
2009 ◽  
Vol 40 (47) ◽  
Author(s):  
Yujiro Hayashi ◽  
Kuppusamy Sankar ◽  
Hayato Ishikawa ◽  
Yuriko Nozawa ◽  
Kazutoshi Mizoue ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Naturally Occurring ◽  
The Absolute
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