Stereocontrolled Formation of Annelated Cyclopentanes by Intramolecular Hetero‐Diels–Alder Reaction. Synthesis of Deoxyloganin from Citronellal | Zendy

Tietze Lutz F. | Zendy; Denzer Horst | Zendy; Holdgrün Xenia | Zendy; Neumann Manfred | Zendy

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Stereocontrolled Formation of Annelated Cyclopentanes by Intramolecular Hetero‐Diels–Alder Reaction. Synthesis of Deoxyloganin from Citronellal

Author(s) -

Tietze Lutz F.,

Denzer Horst,

Holdgrün Xenia,

Neumann Manfred

Publication year - 1987

Publication title -

angewandte chemie international edition in english

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 0570-0833

DOI - 10.1002/anie.198712951

Subject(s) - cyclopentanes , intramolecular force , chemistry , cycloaddition , intermolecular force , citronellal , adduct , stereochemistry , pyran , stereoselectivity , diels–alder reaction , derivative (finance) , catalysis , organic chemistry , molecule , financial economics , economics

An astonishingly highly induced diastercoselectivity (>98%) characterizes the intermolecular cycloaddition of the adduct of 1 and 2 . The cis coupled cyclopenta[c]pyran derivative 3 is formed, which could be converted in six steps into the deoxyloganin 4 . Compound 4 is of interest as a precursor for the biosynthesis of alkaloids.

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