Biomaterial Database

Enantioselective total synthesis of (+)-colletoic acid via catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide. 2013

Takashi Sawada, and Masahisa Nakada

Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.

The enantioselective total synthesis of (+)-colletoic acid, a potent naturally occurring 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor, is described. This total synthesis features a highly enantioselective catalytic asymmetric intramolecular cyclopropanation of an α-diazo-β-keto diphenylphosphine oxide and five highly stereoselective reactions (cyclopropane opening, Diels-Alder reaction, iodolactonization, alkene formation, and reduction of α,β-unsaturated carboxylic acid).

UI	MeSH Term	Description	Entries
D002264	Carboxylic Acids	Organic compounds containing the carboxy group (-COOH). This group of compounds includes amino acids and fatty acids. Carboxylic acids can be saturated, unsaturated, or aromatic.	Carboxylic Acid,Acid, Carboxylic,Acids, Carboxylic
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D003521	Cyclopropanes	Three-carbon cycloparaffin cyclopropane (the structural formula (CH2)3) and its derivatives.
D001391	Azo Compounds	Organic chemicals where aryl or alkyl groups are joined by two nitrogen atoms through a double bond (R-N	Azo Dye,Azo Dyes,Compounds, Azo,Dye, Azo,Dyes, Azo
D012717	Sesquiterpenes	Fifteen-carbon compounds formed from three isoprenoid units with general formula C15H24.	Farnesanes,Farnesene,Farnesenes,Sesquiterpene,Sesquiterpene Derivatives,Sesquiterpenoid,Sesquiterpenoids,Derivatives, Sesquiterpene
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D043205	11-beta-Hydroxysteroid Dehydrogenase Type 1	A low-affinity 11 beta-hydroxysteroid dehydrogenase found in a variety of tissues, most notably in LIVER; LUNG; ADIPOSE TISSUE; vascular tissue; OVARY; and the CENTRAL NERVOUS SYSTEM. The enzyme acts reversibly and can use either NAD or NADP as cofactors.	11 beta-Hydroxysteroid Dehydrogenase Type 1,11beta-HSD1,11beta-HSD1 Reductase,11beta-Hydroxysteroid Dehydrogenase Type 1,11beta HSD1 Reductase,11beta Hydroxysteroid Dehydrogenase Type 1
D043303	Aryldialkylphosphatase	An enzyme which catalyzes the hydrolysis of an aryl-dialkyl phosphate to form dialkyl phosphate and an aryl alcohol. It can hydrolyze a broad spectrum of organophosphate substrates and a number of aromatic carboxylic acid esters. It may also mediate an enzymatic protection of LOW DENSITY LIPOPROTEINS against oxidative modification and the consequent series of events leading to ATHEROMA formation. The enzyme was previously regarded to be identical with Arylesterase (EC 3.1.1.2).	Aryl-dialkyl Phosphatase,Arylalkylphosphatase,Homocysteine Thiolactone Hydrolase,OPA Anhydrase,OPH Enzyme,Organophosphorus Acid Anhydrase,Organophosphorus Acid Anhydrolase,Organophosphorus Acid Hydrolase,Organophosphorus Hydrolase,Paraoxonase,Paraoxonase-1,Paraoxonase-2,Acid Anhydrase, Organophosphorus,Acid Anhydrolase, Organophosphorus,Acid Hydrolase, Organophosphorus,Anhydrase, OPA,Anhydrase, Organophosphorus Acid,Anhydrolase, Organophosphorus Acid,Aryl dialkyl Phosphatase,Enzyme, OPH,Hydrolase, Homocysteine Thiolactone,Hydrolase, Organophosphorus,Hydrolase, Organophosphorus Acid,Paraoxonase 1,Paraoxonase 2,Phosphatase, Aryl-dialkyl,Thiolactone Hydrolase, Homocysteine