Mniopetal E
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01953 |
| CAS | 158761-02-5 |
| Molecular Weight | 296.31 |
| Molecular Formula | C15H20O6 |
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Description
Mniopetal E is a reverse transcriptase inhibitor produced by Mniopetalum sp. 87256.
Specification
| IUPAC Name | (3S,3aS,6aS,9S,10R,10aR)-3,9,10-trihydroxy-7,7-dimethyl-1-oxo-3a,6,6a,8,9,10-hexahydro-3H-benzo[d][2]benzofuran-4-carbaldehyde |
| Canonical SMILES | CC1(CC(C(C23C1CC=C(C2C(OC3=O)O)C=O)O)O)C |
| InChI | InChI=1S/C15H20O6/c1-14(2)5-8(17)11(18)15-9(14)4-3-7(6-16)10(15)12(19)21-13(15)20/h3,6,8-12,17-19H,4-5H2,1-2H3/t8-,9-,10+,11-,12-,15+/m0/s1 |
| InChI Key | FCQQCKZJCMQQPN-DKCZEEBHSA-N |
Properties
| Appearance | Colorless Oil |
| Boiling Point | 548.6±50.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Total synthesis of (-)-mniopetal E, a novel biologically intriguing drimane sesquiterpenoid
Y Suzuki, R Nishimaki, M Ishikawa, T Murata, K I Takao, K I Tadano J Org Chem. 2000 Dec 15;65(25):8595-607. doi: 10.1021/jo001004p.
We have achieved the total synthesis of (-)-mniopetal E, a drimane sesquiterpenoid which inhibits the reverse transcriptase of human immunodeficiency virus (HIV)-1. Our enantiospecific total synthesis of this target molecule in naturally occurring form commenced with a known 2,3-anhydro-D-arabinitol derivative, which was prepared using the Sharpless asymmetric epoxidation strategy. The key steps of our total synthesis were as follows: (1) a combination of highly stereocontrolled inter- and intramolecular Horner-Emmons carbon elongations for construction of a butenolide tethering a 1,2,4, 9-functionalized nona-5,7-diene moiety at the beta-carbon, (2) stereoselective thermal intramolecular Diels-Alder reaction of the thus-formed trienic compound, providing preferentially an endo-cycloadduct with the desired pi-facial selection, and (3) efficient transformation of the gamma-lactone moiety in the major cycloadduct to the gamma-hydroxy-gamma-lactone part in mniopetal E. Our total synthesis of (-)-mniopetal E established the unsettled absolute stereochemistry of the antibiotic.
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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 ╳
