Biomaterial Database

Medium ring ethers by ring expansion-ring contraction: synthesis of lauthisan. 2002

Mark J Coster, and James J De Voss

Department of Chemistry, University of Queensland, Brisbane 4072, Australia.

[reaction: see text] A new general method for the construction of medium ring ethers has been developed. This involves the ring expansion of halo-O,S-acetals followed by a Ramburg-Bäcklund ring contraction reaction with concomitant extrusion of the sulfur atom. This methodology has been utilized for the synthesis of cis- and trans-lauthisan.

UI	MeSH Term	Description	Entries
D007659	Ketones	Organic compounds containing a carbonyl group	Ketone
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D004988	Ethers, Cyclic	Compounds of the general formula R-O-R arranged in a ring or crown formation.	Cyclic Ether,Cyclic Ethers,Ether, Cyclic
D000438	Alcohols	Alkyl compounds containing a hydroxyl group. They are classified according to relation of the carbon atom: primary alcohols, R-CH2OH; secondary alcohols, R2-CHOH; tertiary alcohols, R3-COH. (From Grant & Hackh's Chemical Dictionary, 5th ed)
D001685	Biological Factors	Endogenously synthesized compounds that influence biological processes not otherwise classified under ENZYMES; HORMONES or HORMONE ANTAGONISTS.	Biologic Factors,Biological Factor,Factor, Biologic,Factor, Biological,Factors, Biological,Biologic Factor,Factors, Biologic
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
D013440	Sulfides	Chemical groups containing the covalent sulfur bonds -S-. The sulfur atom can be bound to inorganic or organic moieties.	Sulfide,Thioether,Thioethers,Sulfur Ethers,Ethers, Sulfur
D035964	Oxocins	Compounds based on an 8-membered heterocyclic ring including an oxygen. They can be considered medium ring ethers.	Oxocenes