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Terpene und Terpen‐Derivate, XXI. Synthese von rac ‐4,5‐Dihydro‐β‐curcumen‐4,5‐diol
Author(s) -
Weyerstahl Peter,
MarschallWeyerstahl Helga,
Scholz Stefan
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870864
Subject(s) - terpene , chemistry , hydrolysis , ketone , diol , alcohol , allylic rearrangement , organic chemistry , allylic alcohol , stereochemistry , catalysis
Terpenes and Terpene Derivatives, XXI. – Synthesis of rac ‐4,5‐Dihydro‐β‐curcumene‐4,5‐diol Hydrolysis of the β‐curcumene monoepoxide 1 afforded the title compound 2 . – A second way started from the epoxy ketone 6 . Hydrolysis (→ 7 ), formation of the THP ethers (→ 8 , → 9 ), and reaction with homoprenyllithium leads to the allylic alcohol 3 . After further protection (→ 4 ), Birch reduction, and subsequent hydrolysis a 1:4 mixture of the diols 2 and ( E/Z )‐ 11 was isolated.