Internal and External Stereoisomers of Squaraine Rotaxane Endoperoxide: Synthesis, Chemical Differences, and Structural Revision

2014 ◽  
Vol 79 (3) ◽  
pp. 1120-1130 ◽  
Author(s):  
Carleton G. Collins ◽  
Joshua M. Lee ◽  
Allen G. Oliver ◽  
Olaf Wiest ◽  
Bradley D. Smith
Keyword(s):  
Structural Revision ◽  
Squaraine Rotaxane

Synthetic studies toward inducamide C

2021 ◽  
Author(s):  
Ardalan A. Nabi ◽  
Lydia M. Scott ◽  
Daniel P. Furkert ◽  
Jonathan Sperry
Keyword(s):  
Natural Product ◽  
Structural Revision ◽  
Synthetic Studies

The rare benzoxazepine ring in the alkaloid inducamide C is unstable and prone to rearrangement, indicating that structural revision of the natural product may be necessary.

Structure Revision of Protoaculeine B, a Posttranslationally Modified N-Terminal Residue in the Peptide Toxin Aculeine B

2020 ◽  
Author(s):  
Raku Irie ◽  
Kei Miyako ◽  
Satoko Matsunaga ◽  
Ryuichi Sakai ◽  
Masato Oikawa
Keyword(s):  
Mass Spectra ◽  
Chemical Reactivity ◽  
Model Compounds ◽  
Structural Revision ◽  
Structure Revision ◽  
Peptide Toxin ◽  
One Step ◽  
Marine Peptide ◽  
Synthetic Models ◽  
Long Chain

<div>Here, we newly propose the structure of protoaculeine B, an N-terminal moiety of the marine peptide toxin aculeine B, as possessing the cis-disubstituted tetrahydro-beta-carboline framework. We prepared two truncated model compounds that lack long-chain polyamine by one-step Pictet-Spengler reaction of tryptophan, and compared the NMR and mass spectra and chemical reactivity with those of natural protoaculeine B. The synthetic models reproduced the profiles of the natural product well, which was conclusive for the structural revision.</div>

Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion

2019 ◽  
Author(s):  
Timothy Newhouse ◽  
Alexander Schuppe ◽  
Yizhou Zhao ◽  
Yannan Liu
Keyword(s):  
Total Synthesis ◽  
Inhibitory Activity ◽  
Knoevenagel Condensation ◽  
Cost Effective ◽  
Effective Procedure ◽  
Direct Transformation ◽  
Structural Revision ◽  
Alpha Beta ◽  
Ptp 1B

We report the first total synthesis of (+)-granatumine A, a limonoid alkaloid with PTP-1B inhibitory activity, in 10 steps. Over the course of this study, two key methodological advances were made: a cost effective procedure for ketone alpha,beta-dehydrogenation using allyl-Pd catalysis, and a Pd-catalyzed protocol to convert epoxyketones to 1,3-diketones. The central tetrasubstituted pyridine is formed by a convergent Knoevenagel condensation and carbonyl-selective electrocyclization cascade, which was followed by a direct transformation of a 2<i>H</i>-pyran to a pyridine. These studies have led to the structural revision of two members of this family.

Synthesis and Structural Revision of Glyphaeaside C

2021 ◽  
Author(s):  
Brendan J. Byatt ◽  
Atsushi Kato ◽  
Stephen G. Pyne
Keyword(s):  
Structural Revision

Structural revision of methyl tortuoate D, abis-cembranoid from HainanSarcophyton tortuosumand its absolute stereochemistry

2013 ◽  
Vol 15 (5) ◽  
pp. 566-573 ◽  
Author(s):  
Yu-Fen Li ◽  
Ling-Li He ◽  
Hai-Li Liu ◽  
Lin-Fu Liang ◽  
Hong-Bin Zhang ◽  
...  
Keyword(s):  
Structural Revision ◽  
Absolute Stereochemistry

Conformation-Enabled Total Syntheses of Ohmyungsamycins A and B and Structural Revision of Ohmyungsamycin B

2018 ◽  
Vol 130 (12) ◽  
pp. 3123-3127 ◽  
Author(s):  
Joonseong Hur ◽  
Jaebong Jang ◽  
Jaehoon Sim ◽  
Woo Sung Son ◽  
Hee-Chul Ahn ◽  
...  
Keyword(s):  
Total Syntheses ◽  
Structural Revision

Total synthesis of (±) - isosesquicarene: A structural revision

1983 ◽  
Vol 24 (41) ◽  
pp. 4445-4446 ◽  
Author(s):  
Tadao Uyehara ◽  
Jun-ichi Yamada ◽  
Tadahiro Kato ◽  
Ferdinand Bohlmann
Keyword(s):  
Total Synthesis ◽  
Structural Revision

ChemInform Abstract: Physalins Possessing an Endoperoxy Structure from Physalis alkekengi var. francheti. Structural Revision of Physalin K.

ChemInform ◽  
2010 ◽  
Vol 26 (23) ◽  
pp. no-no
Author(s):  
B. MAKINO ◽  
M. KAWAI ◽  
Y. IWATA ◽  
H. YAMAMURA ◽  
Y. BUTSUGAN ◽  
...  
Keyword(s):  
Structural Revision
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