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Stoffwechselprodukte von Mikroorganismen. 101. Mitteilung. Synthese der trans ‐5‐Hydroxy‐3‐methylpenten‐(2)‐säure ( trans ‐Δ 2 ‐Anhydromevalonsäure)
Author(s) -
KellerSchierlein W.,
Widmer J.,
Maurer B.
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550123
Subject(s) - chemistry , wittig reaction , ketone , intramolecular force , methyl vinyl ketone , derivative (finance) , reagent , condensation , stereochemistry , medicinal chemistry , organic chemistry , catalysis , physics , financial economics , economics , thermodynamics
Abstract trans ‐Δ 2 ‐Anhydromevalonic acid (XVII) was prepared by a Wittig reaction, starting from (4‐tetrahydro‐2‐pyranyloxy)‐2‐butanone. On the other hand, the corresponding 4‐acetoxy‐2‐butanone gave, under similar conditions, the cyclohexene derivative V, explainable by a twofold Michael addition of the Wittig reagent to methyl vinyl ketone, followed by an intramolecular alcol condensation.