Total synthesis of (+)-verrucosidin

Whang, Konghyun; Cooke, R. J.; Okay, G.; K., Jin

doi:10.1021/ja00180a057

Cited by 41 publications

(10 citation statements)

References 2 publications

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“…The absolute configuration of 3 was previously established by organic synthetic studies. [22][23][24] Slight differences in 13 C chemical shifts were detected for the signals due to C-7, C-8 and C-22, which indicated that 1 and 2 were the …”

Section: Absolute Configurations Of Penicyrones a (1) And B (2)mentioning

confidence: 99%

Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.

Yamazaki

Takahashi

et al. 2015

J Antibiot

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Two polyketides containing an α-pyrone unit, named penicyrones A (1) and B (2), were isolated from a culture broth of the marine-derived Penicillium sp. TPU1271 together with nine known compounds: verrucosidin (3), fructigenine A (4), verrucofortine (5), cyclo-(L-Trp-L-Phe) (6), cyclopenol (7), cyclopenin (8), penipratynolene (9), aspterric acid (10) and viridicatol (11). The structures of 1 and 2 were elucidated by analyzing the spectroscopic data of 1, 2 and their O-acetyl derivatives (1a and 2a). Compounds 1 and 2 were epimers of each other at the C-9 position. The absolute configurations of 1 and 2 were assigned on the basis of NOESY data for 1, 2, 1a and 2a, a conformational analysis and the identity of the biogenetic pathway with verrucosidin (3). The planar structure of penicyrones was found in the SciFinder as a compound in the commercial chemical libraries; however, the stereostructure and spectroscopic data were not available. Therefore, this is the first study on the isolation and structure elucidation, including the absolute configurations, of penicyrones A (1) and B (2) as fungal metabolites. Compound 3 exhibited growth inhibitory activity against Mycobacterium smegmatis at 40 μg per disc (inhibition zone of 11 mm). This is the first study to demonstrate that verrucosidin (3) exhibited anti-mycobacterial activity.

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Section: Absolute Configurations Of Penicyrones a (1) And B (2)mentioning

confidence: 99%

Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.

Yamazaki

Takahashi

et al. 2015

J Antibiot

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“…However, heating MICROREVIEW the olefinic mixture at reflux with PdCl 2 (MeCN) 2 in benzene effected isomerization without racemization of the C8 center. [26] Generation of the desired diene partner 8 for the Diels-Alder cyclization was brought about through methylenation of the B-ring ketone with Tebbe's reagent.…”

Section: Danishefsky's Synthesis -Evidence That (+)-Frondosin B Occurmentioning

confidence: 99%

The Frondosins: An Unusual Synthetic and Stereochemical Journey

VanHeyst

Wright

2014

Eur J Org Chem

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Isolated from the marine sponge Dysidea frondosa, the frondosin family of meroterpenoid natural products were shown to be antagonists of the binding of the cytokine interleukin‐8 to its receptor. With implications of interleukin‐8 management being associated with a wide range of acute and chronic inflammatory disorders, as well as tumor progression and/or metathesis, there have been a multitude of syntheses of these natural products in the hopes of developinging new pharmacological agents. However, assignment of the absolute configurations of these natural products became unclear, because the first two syntheses of frondosin B, by Danishefsky and by Trauner, produced conflicting assignments for the single stereogenic center at C8. Here we describe the initial stereochemical mystery surrounding the Danishefsky and Trauner syntheses and provide evidence through ensuing syntheses of frondosins B and A that resolve this issue. These subsequent asymmetric syntheses have established that (1) the natural product occurs as the R enantiomer, and (2) a late‐stage stereochemical inversion occurred during the Trauner and Wright syntheses of frondosin B.

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“…Jeon and Kim [146] Alkyl derivatives of 4-hydroxy-2-pyrones attracted considerable attention because of their broad chemical and biological properties. Synthesis of such, complex natural 2pyrones as verrucosodin [147], citreoviridin [148], citromontanin [149] and many other such compounds cover an extensive area of chemical and biological methods of molecule transformation. Lokot and Pashkovsky [150] r e p o r t e d for the construction of 2-pyrones with various alkyl substituents by thermolysis of acetoacylated Meldrum's acid as a key step for the construction of the 2-pyrone-ring system.…”

Section: Cyanoquinolinesmentioning

confidence: 99%

Cyclic 1,3‐diones and their derivatives—As versatile reactive intermediates in the syntheses of condensed fused ring heterocyles

Sekhar

2004

Journal of Heterocyclic Chem

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Total synthesis of (+)-verrucosidin

Cited by 41 publications

References 2 publications

Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.

Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp.

The Frondosins: An Unusual Synthetic and Stereochemical Journey

Cyclic 1,3‐diones and their derivatives—As versatile reactive intermediates in the syntheses of condensed fused ring heterocyles

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