Garner's aldehyde

Liang, Xifu; Andersch, Jens; Bols, Mikael

doi:10.1039/b101054i

Cited by 140 publications

(61 citation statements)

References 175 publications

(170 reference statements)

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“…31 In this context, we have thought of developing a general synthetic approach for the synthesis of all 2-amino-3-alakanols. Herein, we report the synthesis of clavaminols A, C and H from commercially available Garners aldehyde 32,33 in concise and high overall yields. Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

General synthetic strategy for clavaminols A, C and H

Thirupathi¹,

Bharath²,

Mohapatra³

2015

Arkivoc

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Dedicated to Dr. J. S. Yadav on the occasion of his 65th birthday and in appreciation of his outstanding contributions to synthetic organic chemistry DOI: http://dx.doi.org/10.3998/ark.5550190.p009.281 Abstract A general and efficient synthetic strategy has been developed for the total syntheses of clavaminols A, C and H in 5 to 7 steps starting from (R)-Garners aldehyde following Grignard reaction, Corey-Bakshi-Shibata asymmetric reduction and selective acetylation as key steps with 42 to 59% overall yields, respectively.

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Section: Resultsmentioning

confidence: 99%

General synthetic strategy for clavaminols A, C and H

Thirupathi¹,

Bharath²,

Mohapatra³

2015

Arkivoc

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“…Moreover, the b-alcohol and the a-carboxylic acid gave rise to various side reactions, causing the undesired formation of g-lactams, b-lactones, and anhydrides. Although various strategies for the synthesis of enantioselective threo-b-hydroxy-a-amino acids, such as asymmetric aminohydroxylations, [16] elaboration of serine aldehydes [17] and ketones, [18] and additions of bislactim ether titanium enolates, [19] aziridines, [20] or glycine anion equivalents to aldehydes [21] have been very successful in other cases, none of these methods appeared to be ideal for a large-scale synthesis of orthogonally protected HyGlu. In particular, the question how to regioselectively differentiate between the a-and w-carboxylate functions impeded the use of established methodolo- www.chemmedchem.org gies.…”

Section: Synthesis Of the Non-proteinogenic Amino Acid Precursorsmentioning

confidence: 96%

Total Synthesis and Initial Structure–Activity Relationships of Longicatenamycin A

Nussbaum¹,

Anlauf²,

Freiberg³

et al. 2008

ChemMedChem

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Natural products have provided the majority of lead structures for marketed antibacterials. In addition, they are biological guide principles to new therapies. Nevertheless, numerous “old” classes of antibiotics such as the longicatenamycins have never been explored by chemical postevolution. Longicatenamycin A is the first defined longicatenamycin congener that has been totally synthesized and tested in pure form. This venture required the de novo syntheses of the non‐proteinogenic amino acids (2S,3R)‐β‐hydroxyglutamic acid (HyGlu), 5‐chloro‐D‐tryptophan (D‐ClTrp), and (S)‐2‐amino‐6‐methylheptanoic acid (hhLeu). In the key step, the sensitive HyGlu building block was coupled as a pentafluorophenyl active ester to the unprotected H‐D‐ClTrp‐Glu‐hhLeu‐D‐Val‐D‐(Cbz)Orn‐OH fragment. This first total synthesis of longicatenamycin A provided new congeners of the natural product (deacetyllongicatenamycin, dechlorolongicatenamycin, and longicatenamycin‐A‐amide).

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“…Nitration of 2-methylbenzoxazole gives a 4 : 1 mixture of 6-and 5-nitro derivatives. The typical condensation is conveniently conducted in boiling benzene with continuous removal of water [426] as described for the synthesis of oxazolidine 258, which was then transformed into the Garner aldehyde 259 (a useful synthetic intermediate) (Scheme 10.150) [427].…”

Section: Benzo-13-azolesmentioning

confidence: 99%