Synthesis of crystalline (.+-.)-fecapentaene

Pfaendler, H. R.; Maier, Franz Karl; Klar, S.

doi:10.1021/ja00266a057

Cited by 35 publications

(7 citation statements)

References 1 publication

(1 reference statement)

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“…Synthetic fecapentaene-12 has been prepared by several methods. In addition to those already cited, which yield, respectively, mixtures of E and Z isomers at the 5-position [3,4] the 1-position [3,5] (10), it has been prepared as the 1-Z isomer [5] (11) and the all-E isomer [3] (11,12). The availability of the isomers 3, 4, and 5 enables us to draw the following conclusions about the stereochemistry of natural fecapentaene-12.…”

Section: Ohmentioning

confidence: 97%

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On the Stereochemistry of Fecapentaene-12

Kingston

Piccariello²,

Duh³

et al. 1988

J. Nat. Prod.

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Section: Ohmentioning

confidence: 97%

“…of the stereochemistry of fecapentaene- 12 is, thus, important in the synthesis of appropriate compounds for biological testing.…”

mentioning

confidence: 99%

On the Stereochemistry of Fecapentaene-12

Kingston

Piccariello²,

Duh³

et al. 1988

J. Nat. Prod.

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“…In later studies we and others − synthesized fecapentaene-12, and we also prepared compounds 22 – 25 with varying numbers of double bonds. Unsurprisingly, mutagenic activity decreased with decreasing numbers of double bonds, and the tetraene 25 was 20–30-fold less mutagenic than fecapentaene-12 …”

Section: The Fecapentaenesmentioning

confidence: 99%

My 60-Year Love Affair with Natural Products

Kingston

2021

J. Nat. Prod.

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The author describes his 60-year career in studying the chemistry of natural products, which includes structural, synthetic, and biosynthetic studies of natural products ranging from insect pigments, antibiotics, and fecal mutagens to taxol and other anticancer natural products as well as antimalarial natural products. One of the compounds discussed, napabucasin, is now an anticancer drug in phase III clinical trials.M y career in the study of the chemistry of natural products has been immensely rewarding, with the opportunity to work with and learn from an amazing group of co-workers, some key providential events, and many pleasing discoveries. This article describes selected studies of a variety of natural products in a more or less chronological order, from graduate work in 1960 to retirement in 2020.

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“…The reduction of alk-2-ene-1,4-diols 28 23 or of the respective ethers 29,30 in the system LiAlH 4 ± TiCl 3 was used in the synthesis of retinoids 24 31,32 and other natural products. 30,33 DMAP is 4-dimethyaminopyridine; DBU is 1,8-diazabicyclo- [5.4.0]undec-7-ene; MOM is methoxymethyl; LDA is lithium diisopropylamide. MeC OSiMe3 1.…”

Section: Reductive Eliminationmentioning

confidence: 99%

Synthetic methodologies for carbo-substituted conjugated dienes

Васильев¹,

Serebryakov²

2001

Russ. Chem. Rev.

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We report the observation of changes in the wave turbulence properties of gravitycapillary surface waves due to a finite-depth effect. When the fluid depth is decreased, a hump is observed on the wave spectrum in the capillary regime at a scale that depends on the depth. The possible origin of this hump is discussed. In the gravity regime, the wave spectrum still shows a power law but with an exponent that strongly depends on the depth. A change in the scaling of the gravity spectrum with the mean injected power is also reported. Finally, the probability density function of the wave amplitude rescaled by its rms value is found to be independent of the fluid depth and to be well described by a Tayfun distribution.

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Synthesis of crystalline (.+-.)-fecapentaene

Cited by 35 publications

References 1 publication

On the Stereochemistry of Fecapentaene-12

On the Stereochemistry of Fecapentaene-12

My 60-Year Love Affair with Natural Products

Synthetic methodologies for carbo-substituted conjugated dienes

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