The chemistry of thujone. XX. New enantioselective syntheses of Ambrox and epi-Ambrox
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The development of a new synthetic approach to (−)-Ambrox® (37) and epi-Ambrox® (29) using thujone (1) as a chiral synthon, is presented. Thujone (1), a readily available starting material obtained from Western red cedar, can be efficiently converted to β-cyperone (2) and the latter is then chemically elaborated to the key intermediate, the enone 6. A carbonyl transposition of 6 to enone 9 also allows a formal synthesis of (−)-Polywood® (18). Keywords: thujone, β-cyperone, (−)-Ambrox®, epi-Ambrox®, synthesis.
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2015 ◽
Vol 30
(1)
◽
pp. 57-59
◽
2010 ◽
Vol 30
(3)
◽
pp. 299-314
◽
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