Chemistry of zamoranic acid. Part 10. Homochiral hemisynthesis of pereniporin A

Urones, Julio G.; Dı́ez, David; Gómez, P. M.; Marcos, Isidro S.; Basabe, P.; Moro, Rosalina F.

doi:10.1039/a700377c

Cited by 19 publications

(11 citation statements)

References 4 publications

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“…The overall yields (55% for polygodial and 27% for warburganal) were much better than those previously reported. 233,234 Synthesis of pereniporin B (239) was studied by Urones et al 235 starting with epoxy ester (236) (see Scheme 17).…”

Section: Synthesis Of Drimanes By Transformation Of Natural Productsmentioning

confidence: 99%

“…Allylic oxid-ation introduced the C-6 ketone, which was selectively reduced by sodium borohydride mediated by cerium trichloride. Saponification with base then afforded pereniporin B (239) in 19% yield based on epoxide (236). A similar sequence was undertaken with epoxy acetate (234) (see Scheme 17).…”

Section: Synthesis Of Drimanes By Transformation Of Natural Productsmentioning

confidence: 99%

“…Deprotection with tetrabutylammonium fluoride was followed by hemiacetal formation whereby pereniporin A (242) was obtained in 21% yield based on epoxide (234). 236 The oleoresin of Larix decidua contains large amounts of the labdane diterpene (ϩ)-larixol (171), which can be isolated easily in a pure form. 237 Since it has a hydroxyl group at C-6 as a characteristic structural element, it is particularly suited for the synthesis of drimanes that have a functional group at this position (see Scheme 18).…”

Section: Synthesis Of Drimanes By Transformation Of Natural Productsmentioning

confidence: 99%

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Occurrence, biological activity and synthesis of drimane sesquiterpenoids

2004

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In this review the names, structures and occurrence of all new drimanes and rearranged drimanes which have been published between January 1990 and January 2003 have been collected. Subjects that have been treated are biosynthesis, analysis, biological activities, with special attention to cytotoxic activity and antifeedant and insecticidal activity and mode of action. An important part of the review deals with the synthesis of drimanes. This part has been subdivided into syntheses by transformation of natural products, syntheses starting from chiral compounds obtained by enzymatic resolution, syntheses by cationic polyolefin cyclizations, syntheses from trans-decalones, syntheses by radical cyclizations and syntheses by cycloaddition reactions. The review contains about 350 references.

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Section: Synthesis Of Drimanes By Transformation Of Natural Productsmentioning

confidence: 99%

Section: Synthesis Of Drimanes By Transformation Of Natural Productsmentioning

confidence: 99%

Section: Synthesis Of Drimanes By Transformation Of Natural Productsmentioning

confidence: 99%

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Occurrence, biological activity and synthesis of drimane sesquiterpenoids

2004

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“…44 A homochiral hemisynthesis of the antibiotic pereniporin A, starting from zamoranic acid, has been achieved. 45 Synthetic studies of the mniopetals, a drimane class of sesquiterpenes, have been reported. 46 Enantiospecific syntheses of wiedendiol B and (+)-puupehenone, starting from the diterpene (2)-sclareol, have been accomplished.…”

Section: Bicyclofarnesanementioning

confidence: 99%

Natural sesquiterpenoids

Fraga¹

1999

Nat. Prod. Rep.

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“…The remaining known metabolites were identified by comparing their spectroscopic data with that reported in the literature. 1,[7][8][9][10][11][12] All compounds were evaluated for their cytotoxicities against P388, HL-60, K562 and BEL-7402 cell lines using the sulforhodamine B (SRB) 14) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) 14) methods. Only compound 4 exhibited moderate cytotoxicity against the P388 cell line with IC 50 value of 8.7 mM.…”

Section: )mentioning

confidence: 99%

Drimane Sesquiterpenoids from the Mangrove-Derived Fungus Aspergillus ustus

et al. 2011

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Fungi from mangrove have attracted much attention for their unique living conditions of wave-energy tidal mudflats, high moisture level, high salt concentration and lack of oxygen.1) This fungal group has been widely recognized as rich source of active secondary metabolites.2,3) As part of our ongoing search for novel bioactive compounds from microorganisms isolated from unusual or specialized ecological niches, 4-6) the culture extract of a fungus strain (Aspergillus ustus), isolated from the rhizosphere soil of the mangrove Acrostichum aureurm grown in Guangxi Province of China, showed cytotoxic activity against P388 (mice lymphocytic leukemia) cell line. The chemical composition research on the EtOAc extract of the A. ustus fermentation led us to identify five new drimane sesquiterpenes (1-5) together with 14 known analogues (Fig. 1).1,7-12) Herein, we report the structural elucidations and cytotoxic activities of these metabolites against P388, HL-60 (human promyelocytic leukemia cells), K562 (human erythromyeloblastoid leukemia cells) and BEL-7402 (human hepatoma cells).Compound 1 was obtained as a white powder. The molecular formula was determined as C 16 H 28 O 3 on the basis of its high resolution-electrospray ionization-mass spectra (HR-ESI-MS) peak at m/z 291.1930 [MϩNa] ϩ (Calcd for C 16 C-NMR (distortionless enhancement by polarization transfer (DEPT)) spectrum (Table 2) displayed 16 carbon resonances, assignable to five methyls, four methylenes, three methines and four quaternary carbons. Apart from one degree of unsaturation occupied by a double bond, the remaining two degrees of unsaturation required 1 to contain a bicyclic core ring system. The aforementioned data implied that 1 was a drimane sesquiterpense.13) The NMR resonances were similar to those reported for albrassitriol (20), but replacing one of the OHs by a methoxyl group.13) The structure of 1 was further confirmed by 1 H-1 H correlation spectroscopy (COSY) and heteronuclear multiple bond connectivity (HMBC) correlations (Fig. 2). The connection of C-11 and C-9 was determined by the HMBC correlations from H-11 to C-8 and C-10, and the location of -OCH 3 at C-6 was deduced via a correlation between the methoxy protons and C-6.The relative configuration of 1 was determined by the nuclear Overhauser effect spectroscopy (NOESY) spectrum. Correlations between H-13 and H-1b (eq) and between H-5 and H-1a (ax) suggested a trans-fused decalin nucleus.1) The correlation between H-5 and 6-OCH 3 indicated the configu- Five new drimane sesquiterpenes (1-5) together with 14 known analogues (6-19) were isolated from laboratory cultures of a mangrove-derived fungus Aspergillus ustus. Their structures were established by spectroscopic methods and antitumor activities were evaluated by sulforhodamine B (SRB) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) methods.

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Chemistry of zamoranic acid. Part 10. Homochiral hemisynthesis of pereniporin A

Cited by 19 publications

References 4 publications

Occurrence, biological activity and synthesis of drimane sesquiterpenoids

Occurrence, biological activity and synthesis of drimane sesquiterpenoids

Natural sesquiterpenoids

Drimane Sesquiterpenoids from the Mangrove-Derived Fungus Aspergillus ustus

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