Facile synthesis of the enantiomers of frontalin | Zendy

Blair D. Johnston | Zendy; A. C. Oehlschlager | Zendy

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Facile synthesis of the enantiomers of frontalin

Author(s) -

Blair D. Johnston,

A. C. Oehlschlager

Publication year - 1984

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v84-368

Subject(s) - chemistry , enantiomer , yield (engineering) , chirality (physics) , octane , sharpless asymmetric dihydroxylation , organic chemistry , stereochemistry , sequence (biology) , enantioselective synthesis , catalysis , biochemistry , materials science , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , metallurgy , quark

S-(−)- and R-(+)-frontalin (1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane) were prepared from (E)-2-methyl-2,6-heptadiene-1-ol utilizing the Sharpless asymmetric epoxidation reaction to induce chirality. The six-step synthetic sequence proceeded in approximately 50% overall yield and was found to be suitable for the preparation of multi-gram quantities of either enantiomer with ≥ 90% ee.

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