Shortolide A

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
CAS Number	34331-31-2;
3D model (JSmol)	Interactive image;
ChemSpider	34216765;
PubChem CID	102341086;
UNII	3UD72E6T3Z ;
	InChI 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;
	SMILES [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
Chemical formula	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). Infobox references

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]

Spectroscopic elucidation

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

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

^ 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.
^ ^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.

[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.

[Williams-2] Williams, Russell B (2014). "Diterpenes from endangered goldenrod Solidago shortii". Journal of Natural Products. 77 (6): 1438–1444. doi:10.1021/np500178s. PMID 24922615.

[1]

[2]