Synthesis and structure revision of symplocin A

Shao, Luping; Si, Chang‐Mei; Mao, Zhuo‐Ya; Zhou, Wen; Molinski, Tadeusz F.; Wei, Bang‐Guo; Lin, Guo‐Qiang

doi:10.1039/c7qo00052a

Cited by 9 publications

(5 citation statements)

References 47 publications

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“…Symplocin A 265, a sub-nanomolar cathepsin E inhibitor, had its absolute conguration corrected from 26R, 50R, 51R to 26S, 50S, 51S, following the rst total synthesis of the natural linear peptide, along with two non-natural diastereomers. 144 A total synthesis of the proposed structure of nhatrangin A has been described in the literature. 145 Discrepancies in the spectroscopic data between synthetic and natural nhatrangin A led to the synthesis of six diastereomers of the proposed structure.…”

Section: Cyanobacteriamentioning

confidence: 99%

Marine natural products

et al. 2019

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Section: Cyanobacteriamentioning

confidence: 99%

Marine natural products

et al. 2019

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“…The ready availability of both enantiomers of tert-butanesulfinamide in large-scale processes, the easy deprotection of the amine under mild acidic conditions, and a practical procedure for recycling the chiral auxiliary [4,5] have contributed to the widespread use of these imines as precursors of chiral compounds with a nitrogen atom bonded to a stereogenic center. The amine derivatives, resulting after removal of the tert-butanesulfinyl group, can be transformed into enantioenriched nitrogen-containing heterocycles [6,7] including natural alkaloids [8][9][10][11] and other compounds that show different types of biological activities [12,13]. The way to achieve these transformations is by intramolecular cyclizations, involving the free primary amine, and appropriate reactive positions (those positions bearing a leaving group) in the electrophile or in the carbonyl component of the starting imine (Scheme 1).…”

Section: Intoductionmentioning

confidence: 99%

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Mendes¹,

Costa²,

Yus³

et al. 2021

Beilstein J. Org. Chem.

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The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format.

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“…Right after the publication of our partial work, our colleague Li and the Zhang and Luesch group jointly published the revision of its structure from 30S to 30 R . As a continuation of our interest in developing divergent syntheses of natural products isolated from cyanobacteria and investigating their structure–activity relationships, ,, we quickly looked into the synthesis of 30 R -7 , which confirmed the revised stereochemistry. Herein we present the effective approach to synthesize the revised apratoxin E ( 30 R -7 ) and its three non-natural analogues.…”

Section: Introductionmentioning

confidence: 99%

Divergent Synthesis of Revised Apratoxin E, 30-epi-Apratoxin E, and 30S/30R-Oxoapratoxin E

Mao

Liu

et al. 2017

J. Org. Chem.

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In this report, originally proposed apratoxin E (30S-7), revised apratoxin E (30R-7), and (30S)/(30R)-oxoapratoxin E (30S)-38/(30R)-38 were efficiently prepared by two synthetic methods. The chiral lactone 10, recycled from the degradation of saponin glycosides, was utilized to prepare the key nonpeptide fragment 9. Our alternative convergent assembly strategy was applied to the divergent synthesis of revised apratoxin E and its three analogues. Moreover, ring-closing metathesis (RCM) was for the first time found to be an efficient strategy for the macrocyclization of apratoxins.

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Synthesis and structure revision of symplocin A

Cited by 9 publications

References 47 publications

Marine natural products

Marine natural products

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

Divergent Synthesis of Revised Apratoxin E, 30-epi-Apratoxin E, and 30S/30R-Oxoapratoxin E

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