β-Araneosene

β-Araneosene
Names
	Preferred IUPAC name (3aS,6E,10E,12aS)-6,10,12a-Trimethyl-3-(propan-2-ylidene)-1,2,3,3a,4,5,8,9,12,12a-decahydrocyclopenta[11]annulene
	Other names Dolabellane
Identifiers
CAS Number	166240-51-3;
3D model (JSmol)	Interactive image;
ChemSpider	9876501;
PubChem CID	11701776;
UNII	FEC6HY9PJ7 ;
CompTox Dashboard (EPA)	DTXSID701030401 ;
	InChI InChI=1S/C20H32/c1-15(2)18-12-14-20(5)13-11-17(4)8-6-7-16(3)9-10-19(18)20/h7,11,19H,6,8-10,12-14H2,1-5H3/b16-7+,17-11+/t19-,20-/m1/s1 Key: VSEDLQDFSQWMRG-WSHNDMGWSA-N; InChI=1/C20H32/c1-15(2)18-12-14-20(5)13-11-17(4)8-6-7-16(3)9-10-19(18)20/h7,11,19H,6,8-10,12-14H2,1-5H3/b16-7+,17-11+/t19-,20-/m1/s1 Key: VSEDLQDFSQWMRG-WSHNDMGWBP;
	SMILES C\2=C(/CC[C@@H]1/C(=C(\C)C)CC[C@@]1(C)C/C=C(\C)CC/2)C;
Properties
Chemical formula	C20H32
Molar mass	272.476 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

β-Araneosene is a molecule first isolated in 1975 from the mold Sordaria araneosa by Borschberg.^[1] This unprecedented diterpene framework was given the name “araneosene”. In 1976, the skeletal class was renamed to “dolabellane” due to the isolation of several compounds containing this framework found from the sea hare Dolabella californica.^[1] Since their initial discovery, there are now more than 150 known dolabellanes, mostly isolated from marine sources.^[1]^[2]

Biosynthesis

The exact biosynthetic pathway of β-araneosene is not known; however, like other diterpenes, it is assumed to originate with geranylgeranyl pyrophosphate.^[3] The pyrophosphate dissociates to generate an allylic cation at the tail of the molecule. Next a cascade of cyclizations yields the stable β-araneosene-15-yl cation. Finally, elimination of the adjacent proton yields β–araneosene. It has been proposed that other diterpenes including fusicoccanes, dolastanes, and neodolabellanes also proceed through these intermediates.^[1]

β-Araneosene biosynthesis

References

^ ^a ^b ^c ^d Rodríguez, Abimael; González, Ramírez (1998). "The Structural Chemistry, Reactivity, and Total synthesis of Dolabellane Diterpenes". Tetrahedron. 54 (39): 11683–11729. doi:10.1016/s0040-4020(98)83033-0.
^ Rodríguez, Abimael D.; Wei, Xiaomei; Baran, Peter; Raptis, Raphael G. (28 May 2010). "Dolabellane-Type Diterpenoids with Antiprotozoan Activity from a Southwestern Caribbean Gorgonian Octocoral of the Genus". Journal of Natural Products. 73 (5): 925–934. doi:10.1021/np100074r. PMC 2878742. PMID 20384296.
^ Dewick, Paul M. (2009). Medicinal natural products : A biosynthetic approach (3rd ed.). Chichester: A John Wiley & Sons. ISBN 978-0470741672.

[rod-1] Rodríguez, Abimael; González, Ramírez (1998). "The Structural Chemistry, Reactivity, and Total synthesis of Dolabellane Diterpenes". Tetrahedron. 54 (39): 11683–11729. doi:10.1016/s0040-4020(98)83033-0.

[2nd-2] Rodríguez, Abimael D.; Wei, Xiaomei; Baran, Peter; Raptis, Raphael G. (28 May 2010). "Dolabellane-Type Diterpenoids with Antiprotozoan Activity from a Southwestern Caribbean Gorgonian Octocoral of the Genus". Journal of Natural Products. 73 (5): 925–934. doi:10.1021/np100074r. PMC 2878742. PMID 20384296.

[dewick-3] Dewick, Paul M. (2009). Medicinal natural products : A biosynthetic approach (3rd ed.). Chichester: A John Wiley & Sons. ISBN 978-0470741672.

[1]

[2]

[3]