Biomaterial Database

First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product. 2008

Yoshinari Sawama, and Yuka Sawama, and Norbert Krause

Organic Chemistry II, Dortmund University of Technology, D-44227, Dortmund, Germany.

The first total synthesis of (R,R,R)-bejarol and its (3R,5S,9R)-isomer has been accomplished which confirms the absolute configuration of the natural products. The key step is the gold-catalyzed cycloisomerization of the enantiomerically pure beta-hydroxyallenes 12/13 to the corresponding dihydropyrans 14/15.

UI	MeSH Term	Description	Entries
D007536	Isomerism	The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Isomerisms
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D006046	Gold	A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.
D000466	Alkadienes	Acyclic branched or unbranched hydrocarbons having two carbon-carbon double bonds.	Diolefins,Pentadienes
D001688	Biological Products	Complex pharmaceutical substances, preparations, or matter derived from organisms usually obtained by biological methods or assay.	Biologic,Biologic Drug,Biologic Product,Biological,Biological Drug,Biological Medicine,Biological Product,Biologics,Biopharmaceutical,Natural Product,Natural Products,Biologic Drugs,Biologic Medicines,Biologic Pharmaceuticals,Biologic Products,Biological Drugs,Biological Medicines,Biologicals,Biopharmaceuticals,Products, Biological,Drug, Biologic,Drug, Biological,Drugs, Biologic,Drugs, Biological,Medicine, Biological,Medicines, Biologic,Medicines, Biological,Pharmaceuticals, Biologic,Product, Biologic,Product, Biological,Product, Natural
D012717	Sesquiterpenes	Fifteen-carbon compounds formed from three isoprenoid units with general formula C15H24.	Farnesanes,Farnesene,Farnesenes,Sesquiterpene,Sesquiterpene Derivatives,Sesquiterpenoid,Sesquiterpenoids,Derivatives, Sesquiterpene