Diterpenes from Salvia breviflora☆

Cuevas, Gabriel; Collera, Ofelia; García, F; Cárdenas, Jorge; Maldonado, Emma; Ortega, Alfredo

doi:10.1016/s0031-9422(00)81749-5

Cited by 17 publications

(8 citation statements)

References 5 publications

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“…The chosen absolute stereochemistry is that of the compounds from A . dracunculoids for which it was established. , An example of a trans -clerodane with a C-2 to C-18 ether link is brevifloralactone from Salvia breviflora and Salvia melissodora (Labiatae) 1 Selected NOE enhancements, in percent, from difference spectroscopy for amphiacrolide K ( 2 ) at 270 MHz in CDCl 3 . …”

Section: Resultsmentioning

confidence: 99%

“…The chosen absolute stereochemistry is that of the compounds from A. dracunculoids for which it was established. 1,2 An example of a trans-clerodane with a C-2 to C-18 ether link is brevifloralactone from Salvia breviflora 5 and Salvia melissodora (Labiatae). 6 Amphiacrolide L (3), mp 182-184 °C, with a molecular formula C 20 H 26 O 5 , as supported by HRMS, has eight degrees of unsaturation.…”

Section: Resultsmentioning

confidence: 99%

“…(Asteraceae) of the southwestern United States has been already recorded to yield 14 cisclerodane lactones from the aerial parts. 1,2 This report is on five such diterpenes, amphiacrolides J (1), K (2), L (3), M (4), and N (5). All are new natural products, except amphiacrolide N (5), which was reported from another source, 3 but with limited physical data.…”

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confidence: 99%

“…1,2 This report is on five such diterpenes, amphiacrolides J (1), K (2), L (3), M (4), and N (5). All are new natural products, except amphiacrolide N (5), which was reported from another source, 3 but with limited physical data. All of these compounds possess the ethyl butenolide side chain as supported by characteristic MS fragments (m/z 111, 98, and 97) and 1 H-and 13 C-NMR peaks.…”

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confidence: 99%

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cis-Clerodane Diterpene Lactones from Amphiachyris dracunculoides. 3

Harraz

Doskotch

1996

J. Nat. Prod.

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Five cis-clerodane lactones, amphiacrolides J (1), K (2), L (3), M (4), and N (5), were isolated from the aerial parts of the composite Amphiachyris dracunculoides. The first four are new compounds, and the fifth was previously reported from another source. All compounds were assigned stereochemical structures based upon spectral and chemical data, including high-field 1D and 2D NMR for complete assignment of 1H- and 13C-NMR spectra. Amphiacrolide N (5) was converted to amphiacrolide J (1) by treatment with MeOH and TFA, and amphiacrolide L (3) was prepared from amphiacrolide B (9) by CrO3 oxidation to ketone 10 followed by its reduction with NaBH4.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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cis-Clerodane Diterpene Lactones from Amphiachyris dracunculoides. 3

Harraz

Doskotch

1996

J. Nat. Prod.

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“…4 These remarkable bioactivities made these compounds to be attractive synthetic targets. Interestingly, brevifloralactone 2a, a naturally occurring clerodane-type diterpene isolated in large quantities from the aerial part of Salvia breviflora, 5 contains the central core of the hawtriwaic natural product family. It is obvious that a pyran ring opening process in this molecule would afford a compound closely related to 1a-c which might serve as starting material for the synthesis of other analogs or other minor biologically active natural clerodane diterpenes.…”

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confidence: 99%