Biomaterial Database

Stereodivergent route to the carbocyclic core of 2',3'-olefinic carbanucleosides: toward the synthesis of (L)-(+)- and (D)-(-)-carbovir. 2011

Angshuman Chattopadhyay, and Sibanarayan Tripathy

Bio-Organic Division, Bhabha Atomic Research Center, Mumbai, India. achat@barc.gov.in

(R)-2,3-Cyclohexylideneglyceraldehyde (1) has been elegantly exploited for a stereodivergent construction of the potential precursors (11a and 11b) of (L)-(+)- and (D)-(-)-carbovirs, respectively. The key steps in this approach were Luche's allylation of formaldehyde with allylic bromide 4c to produce 5 and ring-closing metathesis of 10b using Grubbs' first-generation catalyst to obtain 11. The moderate stereoselectivity of Luche's allylation reaction resulted in attaining stereodivergence in this approach which could be realized finally through easy chromatographic separation of the two isomers of the metathesis product to obtain homochiral precursors 11a and 11b in good amounts.

UI	MeSH Term	Description	Entries
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
D015224	Dideoxynucleosides	Nucleosides that have two hydroxy groups removed from the sugar moiety. The majority of these compounds have broad-spectrum antiretroviral activity due to their action as antimetabolites. The nucleosides are phosphorylated intracellularly to their 5'-triphosphates and act as chain-terminating inhibitors of viral reverse transcription.	2',3'-Dideoxynucleosides,Dideoxyribonucleosides,ddNus,2',3' Dideoxynucleosides
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