Shortolide A is a natural product isolated from Solidago shortii.[1] S. shortii is an endangered species native to the United States. Shortolide A is one of six diterpenes isolated from the species Solidago shortii. Three of these products are hydrolysis products. Solidago is common across North America but Solidago shortii is only found in a limited area where only 14 wild populations are known. Because of this, the species was designated as endangered.[2]

Shortolide A
Names
Preferred IUPAC name
(1aR,3aS,4S,5S,6S,7aR)-4,5,7a,7b-Tetramethyl-4-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydrooxireno[2,3-a]naphthalen-6-yl (2Z)-2-methylbut-2-enoate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C25H36O5/c1-7-15(2)22(27)29-18-13-24(5)19(8-9-20-25(24,6)30-20)23(4,16(18)3)11-10-17-12-21(26)28-14-17/h7,12,16,18-20H,8-11,13-14H2,1-6H3/b15-7-/t16-,18+,19+,20-,23-,24-,25-/m1/s1
    Key: URRSOXWGRAMYOW-GACOYEMDSA-N
  • [H][C@@]12CC[C@H]3O[C@@]3(C)[C@]1(C)C[C@H](OC(=O)C(\C)=C/C)[C@@H](C)[C@@]2(C)CCC1=CC(=O)OC1
Properties
C25H36O5
Molar mass 416.558 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Spectroscopic elucidation

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Shorotolide A is a colorless solid and is optically active. According to mass spectrometry and NMR the chemical formula is C25H36O5. ROESY correlations were used to determine the relative configuration. The absolute configuration was determined the comparison of calculated and experimental vibrational circular dichroism. Comparisons of calculated and experimental optical rotation was also used.[2]

Proposed Synthesis

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A proposed synthesis is shown below.

 
Shortolide A Proposed synthesis Scheme 1
 
Shortolide A Proposed synthesis Scheme 2
 
Shortolide A Proposed synthesis Scheme 3

References

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  1. ^ Anthonsen, Thorleif; Bergland, Gudrun (1971). "Diterpenoids of some Solidago [goldenrod] species". Acta Chemica Scandinavica. 25 (5): 1924–1925. doi:10.3891/acta.chem.scand.25-1924.
  2. ^ a b Williams, Russell B (2014). "Diterpenes from endangered goldenrod Solidago shortii". Journal of Natural Products. 77 (6): 1438–1444. doi:10.1021/np500178s. PMID 24922615.