The Synthesis of Streptogramin Antibiotics: (−)-Griseoviridin and Its C-8 Epimer

Dvorak, Curt A.; Schmitz, William J.; Poon, Daniel J.; Pryde, David C.; Lawson, Jon P.; Amos, Richard A.; Meyers, A. I.

doi:10.1002/(sici)1521-3757(20000502)112:9<1730::aid-ange1730>3.0.co;2-8

Cited by 35 publications

(8 citation statements)

References 22 publications

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“…Griseoviridin (29), a member of the streptogramin family of antibiotics, currently licensed in the USA against bacteria resistant to vancomycin, has been synthesized [182] for the first time after two decades of endeavour by many groups. The oxazole carboxamide link was chosen for macrolactamization using EDCI/HOBt.…”

Section: Cyclic Peptides Containing Thiazole/oxazole Ringsmentioning

confidence: 99%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

417

241

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Constricting the peptide backbone into a more defined conformational form through cyclization is an activity evolved in nature and in synthetic work, the latter straddling only the most recent decades. The resulting conformational constraints increase the probability of an optimum response with bio-receptors. The purpose of this review is to highlight developments that have proved to be reasonably efficient in the macrocyclization of linear precursors into cyclic peptides and depsipeptides.

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Section: Cyclic Peptides Containing Thiazole/oxazole Ringsmentioning

confidence: 99%

The cyclization of peptides and depsipeptides

Davies

2003

Journal of Peptide Science

417

241

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“…Bond Angles for 0961_PQ_Snyder_2. C15 O3 C7 116.61(12) C7 C8 C12 111.87(12) C1 N1 C11 117.06(13) C9 C8 C7 113.61(13) C1 N1 C12 119.00(12) C9 C8 C12 112.27(13) C12 N1 C11 118.21(12) C10 C9 C8 108.45(13) O1 C1 N1 121.23(15) C11 C10 C9 111.91(13) O1 C1 C2 120.37(15) N1 C11 C10 111.66(13) N1 C1 C2 118.40(13) N1 C12 C4 112.30(12) C3 C2 C1 122.82(15) N1 C12 C8 111.42(12) C2 C3 C4 119.58(14) N1 C12 C13 111.18(12) O2 C4 C3 106.97(12) C4 C12 C8 107.91(12) O2 C4 C5 114.03(12) C13 C12 C4 101.74(11) O2 C4 C12 110.44(12) C13 C12 C8 111.88(12) C3 C4 C5 114.44(12) C12 C13 C14 104.73(11) C3 C4 C12 110.47(12) C13 C14 C5 104.43(11) C12 C4 C5 100.42(11) C15 C14 C5 111.72(12) C4 C5 C14 104.41(11) C15 C14 C13 104.42(12) C6 C5 C4 108.15(12) C15 C14 C16 110.77(12) C6 C5 C14 109.50(12) C16 C14 C5 113.16(12) C7 C6 C5 106.49(12) C16 C14 C13 111.86(12) O3 C7 C6 106.94(12) O3 C15 C14 115.71(13) O3 C7 C8 113.67(13) O4 C15 O3 118.82(15) C6 C7 C8 112.76(13) O4 C15 C14 125.12(15) …”

mentioning

confidence: 99%

“…First, although the ketone moiety within 20 was formally needed to realize the targets ( vide infra ), its presence inflicted undesirable instability within all related intermediates, thus requiring the C-12 ketone to be stereospecifically reduced and protected over two steps to afford 21 ( Scheme 3 ). Next, the allyl ester was selectively cleaved through the action of Pd(PPh 3 ) 4 and pyrrolidine, 15 allowing for the highly hindered bridgehead nitrogen-containing center to then be forged through a Curtius rearrangement conducted under Fukuyama’s conditions, 16 delivering the Boc-protected amine 22 . With an eye toward forming the bridged lactone of the annotinolides, the nitrile group was then converted into a carboxylic acid via a standard reduction/Pinnick oxidation sequence to afford 23 in 81% overall yield.…”

mentioning

confidence: 99%

Concise and Stereoselective Total Syntheses of Annotinolides C, D, and E

Snyder

2021

J. Am. Chem. Soc.

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The annotinolides are one of the most recent additions to the Lycopodium family of alkaloids, with its members possessing challenging, caged structures that include a [3.2.1]-bicyclic core bearing six contiguous stereocenters, including oxa-, aza-, and all-carbon quaternary centers. Herein, we document a concise and stereoselective route that achieves the first total syntheses of three of its members: annotinolides C, D, and E. Key operations include a gold(I)-catalyzed Conia-ene reaction that fashions much of the main core in a single operation, as well as a number of other challenging and chemoselective transformations to generate the remaining elements. Moreover, efforts utilizing the natural products themselves, seeking adjustments in their oxidation states and the rearrangement of individual ring systems, sheds light on their potential biogenesis with some outcomes counter to those originally proposed. Finally, formal enantioenriched syntheses of the target molecules are also presented. File list (2) download file view on ChemRxiv AnnotinolidesTSDraftFinalPreTemplate.pdf (511.47 KiB) download file view on ChemRxiv AnnotinolidesTSSupportingInformationFinalComplete.pdf (8.91 MiB) Concise and Stereoselective Total Syntheses of Annotinolides C, D, and E

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“…First, although the ketone moiety within 20 was formally needed to realize the targets (vide infra), its presence inflicted undesirable instability within all related intermediates, thus requiring the C-12 ketone to be stereospecifically reduced and protected over two steps to afford 21 (Scheme 3). Next, the allyl ester was selectively cleaved through the action of Pd(PPh3)4 and pyrrolidine, 15 allowing for the highly hindered bridgehead aza-quaternary nitrogen center to then be forged through a Curtius rearrangement conducted under Fukuyama's conditions, 16 delivering the Boc-protected amine 22. With an eye towards forming the bridged lactone of the annotinolides, the nitrile group was then converted into a carboxylic acid via a standard reduction/Pinnick oxidation sequence to afford 23 in 95% overall yield.…”

mentioning

confidence: 99%

Concise and Stereoselective Total Syntheses of Annotinolides C, D, and E

Qü¹,

Snyder²

2021

Preprint

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The annotinolides are one of the most recent additions to the <i>Lycopodium</i> family of alkaloids, with its members possessing challenging, caged structures that include a [3.2.1]-bicyclic core bearing six contiguous stereocenters, including oxa-, aza-, and all-carbon quaternary centers. Herein, we document a concise and stereoselective route that achieves the first total syntheses of three of its members: annotinolides C, D, and E. Key operations include a gold(I)-catalyzed Conia-ene reaction that fashions much of the main core in a single operation, as well as a number of other challenging and chemoselective transformations to generate the remaining elements. Moreover, efforts utilizing the natural products themselves, seeking adjustments in their oxidation states and the rearrangement of individual ring systems, sheds light on their potential biogenesis with some outcomes counter to those originally proposed. Finally, formal enantioenriched syntheses of the target molecules are also presented.

show abstract

The Synthesis of Streptogramin Antibiotics: (−)-Griseoviridin and Its C-8 Epimer

Cited by 35 publications

References 22 publications

The cyclization of peptides and depsipeptides

The cyclization of peptides and depsipeptides

Concise and Stereoselective Total Syntheses of Annotinolides C, D, and E

Concise and Stereoselective Total Syntheses of Annotinolides C, D, and E

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