Nuclear Overhauser effect, a unique method of defining the relative stereochemistry and conformation of taxane derivatives

1968 ◽  
Vol 90 (2) ◽  
pp. 522-523 ◽  
Author(s):  
Marion C. Woods ◽  
Hung-Che. Chiang ◽  
Yasuhiro. Nakadaira ◽  
Koji. Nakanishi
Keyword(s):  
Nuclear Overhauser Effect ◽  
Overhauser Effect ◽  
Relative Stereochemistry ◽  
Unique Method ◽  
Nuclear Overhauser

Studies of Australian Soft Corals. XLVI. New Diterpenes From a Briareum Species (Anthozoa, Octocorallia, Gorgonacea)

1989 ◽  
Vol 42 (10) ◽  
pp. 1705 ◽  
Author(s):  
BF Bowden ◽  
JC Coll ◽  
IM Vasilescu
Keyword(s):  
High Field ◽  
Nuclear Overhauser Effect ◽  
Soft Corals ◽  
Overhauser Effect ◽  
Relative Stereochemistry ◽  
Nuclear Overhauser ◽  
New Compounds

The structures and relative stereochemistry of nine new briaran -based diterpenes from a Briareum species have been deduced from 2-D n.m.r. experiments at high field, and nuclear Overhauser effect experiments. The new compounds are (1R*2R*,3R*,5Z,7S*,8S*,9S*,10S*,11R*,-12S*,14S*,17R*)-2,3,14-triacetoxy-8,17:11,12-bisepoxy-9-hydroxybriar-5-en-18-one (5), (1R* ,2R* ,3R* ,5Z*,7S*,8S* ,9S*,10S*,11R*,12S*, 14S*, 17R*)-3,14-diacetoxy-2-butyryloxy-8,17:11,12-bisepoxy-9-hydroxybriar-5-en-18-one (6),(1R*,2R*,3R*,5Z,7S*,8S*,9S*,10S*,11R*,12S*,14S)-2,3,14-triacetoxy-11,12-epoxybriara-5,8(17)-dien-18-one(17),(1S*,2S*,4R*,5Z,7S*,8S*,9S*,10S*,2,4,9.12-tetraacetoxy-8,17-epoxy-11-hydroxybriara-5,13-dien-18-one (8),(1S*, 2S*,4R*, 5Z,7S*,8S*,9S*,10S*, 11S*, 12R*,13Z,17R*)-2,4,9-triacetoxy-8,17-epoxy-11,12-dihydroxybriara-5,13-dien-18-one (9), (1S *,2S*,4R*,5Z,7S*,8S*,9S*,10S*, 11S *,12R*,13Z,17R*)-2,4,9,12-tetraacetoxy-8,17-epoxy-11-hydroxybriara-5,13-dien-18-one(10),(1Si,2S*,5Z,7S',8S*,-9S*,10S*,11R*,12R*,13Z,17R*)-2,12-diacetoxy-8,17-epoxy-9-hydroxybriara-5,13-dien-18-one(ll), (1R*,2R*,3Si,5Z,7S* ,8S* ,9S* ,10S* ,11Z,14S*,17R*)-2,14-diacetoxy-3-butyryloxy-8,17-epoxy-9-hydroxybriara-5,11-dien-18-one (12) and (1R *,2R*,3S*,5Z,7S*,8S*,9S*,10S*,11Z,-14S',17R*)-2,3,14-triacetoxy-8,17-epoxy-9-hydroxybriara-5,11-dien-18-one (13). In addition to the nine new briaran derivatives, the same coral afforded two cladiellane derivatives (1R*,4R*,5S*,6R*,8R*,12R*,13R*,14R*)-cladiellane-4,8,12-triol (14) and its 4-acetoxy derivative (15). Aknowncembranoid diterpene (1R *,4R*,ZE,7E,l1E)-cembra-2,7,11-trien-4-ol(21) wasalso isolated together with an unprecedented perhydrophenanthrene-based diterpene (20): (1R *, 1aR*,4S*,4aR*,5aR*,8aR*)-4-isopropyl-l,8a-dimethyl-5-methylenetetradecahydrophenanthren-1-ol. The extraordinary biosynthetic ability of soft corals from the genus Briareum is once more revealed.

1H NMR studies of [N-MeAib1, Tyr(Me)4]ANGII and [N-MeAib1, Tyr(Me)4, Ile8]ANGII in dimethylsulfoxide by nuclear Overhauser effect (NOE) enhancement spectroscopy: cis-trans Isomerism of the His-Pro bond

1990 ◽  
Vol 55 (4) ◽  
pp. 1106-1111 ◽  
Author(s):  
John Matsoukas ◽  
Paul Cordopatis ◽  
Raghav Yamdagni ◽  
Graham J. Moore
Keyword(s):  
1H Nmr ◽  
Nuclear Overhauser Effect ◽  
Nmr Studies ◽  
Restricted Rotation ◽  
Overhauser Effect ◽  
Major Isomer ◽  
Conformational Properties ◽  
Nuclear Overhauser

The conformational properties of the Sarmesin analogues [N-MeAib1, Tyr(Me)4]ANGII and [N-MeAib1, Tyr(Me)4, Ile8]ANGII in hexadeutero-dimethysulfoxide were investigated by Nuclear Overhauser Effect (NOE) Enhancement Studies. Cis-trans isomers (ratio 1 : 6) due to restricted rotation of the His-Pro bond were observed. Interresidue interactions between the His Cα proton and the two Pro Cδ protons revealed that the major isomer was the trans.

scholarly journals Cylindromicin from Arctic-Derived Fungus Tolypocladium sp. SCSIO 40433

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1080
Author(s):  
Imran Khan ◽  
Jing Peng ◽  
Zhuangjie Fang ◽  
Wei Liu ◽  
Wenjun Zhang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Nuclear Overhauser Effect ◽  
Inhibition Activity ◽  
Tyrosinase Inhibition ◽  
Bioactive Natural Products ◽  
Chemical Structures ◽  
Overhauser Effect ◽  
Spectroscopic Analyses ◽  
Potential Resource ◽  
Nuclear Overhauser

The fungus strain SCSIO 40433 was isolated from an Arctic-derived glacier sediment sample and characterized as Tolypocladium cylindrosporum. A new compound, cylindromicin (1), and seven known secondary metabolites (2–8) were isolated from this strain. The chemical structures of these compounds were elucidated by comprehensive spectroscopic analyses. Cylindromicin (1) featured a 3,4-dihydro-2H-pyran skeleton. The absolute configuration of compound 1 was assigned via interpretation of key Nuclear Overhauser Effect Spectroscopy (NOESY) correlations and Electronic Circular Dichroism (ECD) calculation. Cylindromicin (1) exhibited significant tyrosinase inhibition activity. This study highlights Polar fungi as a potential resource for new bioactive natural products.

The isolation, structure, and stereochemistry of traversiadiene. The precursor hydrocarbon of traversianal biosynthesis

1989 ◽  
Vol 67 (8) ◽  
pp. 1302-1304 ◽  
Author(s):  
Albert Stoessl ◽  
G. L. Rock ◽  
J. B. Stothers
Keyword(s):  
Magnetic Resonance ◽  
Biosynthetic Pathway ◽  
Nuclear Overhauser Effect ◽  
Difference Spectra ◽  
Heteronuclear Correlation ◽  
Magnetic Resonance Studies ◽  
Overhauser Effect ◽  
Effect Difference ◽  
Nuclear Overhauser ◽  
Magnetic Resonance Spectra

A tricyclic diene, traversiadiene, isolated from cultures of Cercosporatraversiana has been shown to have the structure and stereochemistry of the previously postulated hydrocarbon intermediate on the biosynthetic pathway to traversianal (1). Detailed:1H and 13C magnetic resonance studies, including homo- and heteronuclear correlation spectra, led to the gross structure, and the stereochemistry was established through a series of nuclear Overhauser effect difference spectra. Keywords: diterpene, traversiadiene, 1H and 13C magnetic resonance spectra.

scholarly journals Contribution of blood to nuclear Overhauser effect at −1.6 ppm

2021 ◽  
Author(s):  
Jing Cui ◽  
Yu Zhao ◽  
Feng Wang ◽  
Daniel F. Gochberg ◽  
Zhongliang Zu
Keyword(s):  
Nuclear Overhauser Effect ◽  
Overhauser Effect ◽  
Nuclear Overhauser
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