Dihydroepiepoformin
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| Category | Bioactive by-products |
| Catalog number | BBF-01407 |
| CAS | |
| Molecular Weight | 142.15 |
| Molecular Formula | C7H10O3 |
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Description
Dihydroepiepoformin is produced by the strain of Penicillum patulum. It inhibited IL-1 activity with IC50 of 100 μg/mL.
Specification
| IUPAC Name | (1R,3R,5S,6R)-5-hydroxy-3-methyl-7-oxabicyclo[4.1.0]heptan-2-one |
| Canonical SMILES | CC1CC(C2C(C1=O)O2)O |
| InChI | InChI=1S/C7H10O3/c1-3-2-4(8)6-7(10-6)5(3)9/h3-4,6-8H,2H2,1H3/t3-,4+,6-,7+/m1/s1 |
| InChI Key | PISNTDRJPKNUJM-LCZOEFHHSA-N |
Reference Reading
1. Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin
M Carmen Carreño, Estíbaliz Merino, María Ribagorda, Alvaro Somoza, Antonio Urbano Org Lett. 2005 Mar 31;7(7):1419-22. doi: 10.1021/ol050287a.
[reaction: see text] The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the stereocontrolled conjugate addition of AlMe3 to p-quinol 3 and retrocondensation to the ketone functionality, previous to oxidation of the beta-hydroxy sulfoxide moiety of advanced intermediates to the corresponding sulfone.
2. Enantioselective synthesis of natural polyoxygenated cyclohexanes and cyclohexenes from [(p-tolylsulfinyl)methyl]-p-quinols
M Carmen Carreño, Estíbaliz Merino, María Ribagorda, Alvaro Somoza, Antonio Urbano Chemistry. 2007;13(4):1064-77. doi: 10.1002/chem.200601330.
Exploitation of the beta-hydroxysulfoxide fragment present in a number of enantiomerically pure (SR)- and (SS)-[(p-tolylsulfinyl)methyl]-p-quinols allowed chemo- and stereocontrolled conjugate additions of different organoaluminium reagents to the cyclohexadienone moiety. The same fragment was also shown to act as an efficient chiral masking carbonyl group, after oxidation to sulfone and retroaddition in basic medium, with elimination of methyl p-tolyl sulfone. Through the use of both transformations as key steps, enantiocontrolled syntheses of different natural products-such as the two enantiomers of dihydroepiepoformin, (-)-gabosine O, (+)-epiepoformin, (-)-theobroxide and (+)-4-epigabosine A (an epimer of the natural product gabosine A)-has been achieved. The presence of the beta-hydroxy sulfone moiety makes the cyclic structures rigid, allowing a number of stereoselective transformations such as carbonyl reductions, enone epoxidations or cis-dihydroxylations, en route to the natural structures. The observed selectivities were dependent on the particular substitution in each substrate, providing evidence of a strong influence of remote groups on the preferred approach of the reactants to the reactive conformations. An advanced precursor of natural (+)-harveynone was also synthesized, but the isolation of the natural product was not possible because of the instability of the corresponding enone, containing a triple bond, under the basic conditions necessary to eliminate the beta-hydroxy sulfone. This demonstrated that the limitations of the use of the beta-hydroxy sulfoxide as a chiral protecting carbonyl group were dependent on the relative stabilities of the final targets in the presence of the required base.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
