Antibiotics from Polyangium cellulosum var. fulvum. 2. 5-epi-5,6-Dihydroxypolyangioic acid

Connor, David T.; Strandtmann, M. Von

doi:10.1021/jo00418a014

Cited by 27 publications

(13 citation statements)

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“…[9] Its complete structure was determined by elegant spectroscopic analyses, [10] degradative studies and chemical transformation, and by a single X-ray of a derivative.…”

Section: Introductionmentioning

confidence: 99%

New Aspects in the Stereoselective Ethynylation of β‐C‐Glycoside Aldehydes. Application to the Synthesis of an Ambruticin Fragment

et al. 2003

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Stereoselective ethynylation of functionalized β‐C‐glycosyl aldehydes has been achieved with various organometallic alkynes. The diastereoselectivity is highly dependent on the organometallic alkyne and on the functionalization on the C‐6 position of the glycoside. The stereoselective reaction conducted with ester‐functionalized aldehyde, followed by Mitsunobu reaction and two Pd‐catalyzed regio‐ stereo‐ and enantioselective alkylations afforded the “western” part of ambruticin. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…[9] Its complete structure was determined by elegant spectroscopic analyses, [10] degradative studies and chemical transformation, and by a single X-ray of a derivative.…”

Section: Introductionmentioning

confidence: 99%

New Aspects in the Stereoselective Ethynylation of β‐C‐Glycoside Aldehydes. Application to the Synthesis of an Ambruticin Fragment

et al. 2003

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“…The catalyst was filtered off and washed with ethanol. The filtrate and washings were evaporated to give a colorless oil (homogeneous by TLC) (5 mg, 49%); IR (film) 3600 3200 cm-1 (OH); mass spectrum m/e (relative intensity) 468 (3), 466 (4), 450 (8), 432 (2), 407 (3), 344 (8), 337 (37), 319 (11), 269 (6), 253 (10), 167 (40), 154 (50), 127 (100). Found: M+ 468.3718; C28H52O5 requires 468.3814.…”

Section: Preparation Of Octahydrotriolmentioning

confidence: 99%

Antifungal agents. 3. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. A divinylcyclopropane-cycloheptadiene rearrangement.

Connor¹,

Klutchko²,

Strandtmann³

1979

J. Antibiot.

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The thermal rearrangement of antifungal antibiotic 1, isolated from Polyangiwn cellulosum var. fulvium, to cycloheptadiene derivative 2 is described. We recently described1,2) the isolation and structure elucidation of two antifungal antibiotics from Polrangirum cellulosum var. fultiwm. The antibiotics were highly active against pathogenic fungi such as Histoplasma capsulatum and Coccidioides immitis. In a search for new antifungal antibiotics by chemical modification and to gain structural information, antibiotic 11) was thermally rearranged to cycloheptadiene derivative 2 in diphenyl ether at 240-C. It is well known3) that divinylcyclopropanes rearrange to cycloheptadienes and that cis divinylcyclopropanes rearrange at room temperature. Acid 1 is probably the most complex divinylcyclopropane to be transformed to the corresponding cyclohepta.diene. The rearrangement product, acid 2, had greater TLC mobility than 1, but gave a similar mass spectrum fragmentation pattern with a molecular ion at 474 (C28H42O6). Acid 2 was converted to monomethyl ester 3, diacetate 4 and trio] 5. In these reactions the behavior of 2 parallels that of 1. The products (3, 4 and 5) had greater TLC mobility than the corresponding products from 1. Acid 2 and its derivatives showed a strong M-195 peak as well as a strong 193 peak, whereas 1 and its derivatives showed a strong 193 peak but a much weaker M-195 peak. This was the only major difference in the mass spectra of the two sets of compounds. The 1H NMR spectrum of diacetate 4

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“…The ambruticin family of polyketide natural products, first isolated from the myxobacterium Sorangium cellulosum in 1977, display potentially useful biological properties, including significant antifungal activity. [1][2][3][4][5][6][7][8] Studies of the mechanism of action of these compounds suggest that the ambruticins interfere with fungal osmoregulation by targeting the Hik1 kinase. [9,10] A recent study of the effect of ambruticin VS3 on soil myxobacteria confirms an impact on a group III hybrid histidine kinase (HHK) and provides an environmental advantage by affecting the development of competitive myxobacterial species.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J

Trentadue

Chang

Nalin

et al. 2021

Chemistry A European J

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The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.

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Antibiotics from Polyangium cellulosum var. fulvum. 2. 5-epi-5,6-Dihydroxypolyangioic acid

Abstract: An antifungal antibiotic, 5-epi-5,6-dihydroxypolyangioic acid (1), has been isolated from Polyangium celluosum var. fulvum and its structure elucidated by a comparison of the NMR spectra of diacetates 3 and 6, and by conversion of 5,6-dihydroxypolyangioic acid (4) into 1.

Cited by 27 publications

References 0 publications

New Aspects in the Stereoselective Ethynylation of β‐C‐Glycoside Aldehydes. Application to the Synthesis of an Ambruticin Fragment

New Aspects in the Stereoselective Ethynylation of β‐C‐Glycoside Aldehydes. Application to the Synthesis of an Ambruticin Fragment

Antifungal agents. 3. Chemical modification of antibiotics from Polyangium cellulosum var. fulvum. A divinylcyclopropane-cycloheptadiene rearrangement.

Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J

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