Journal
SYNTHESIS-STUTTGART
Volume -, Issue 23, Pages 3639-3646Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2007-990850
Keywords
hydrolytic kinetic resolution; PMB acetal formation; Sharpless asymmetric epoxidation; lactonization; one-pot oxidation/alkenation; esterification
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A simple and efficient stereoselective total synthesis of tarchonanthuslactone and formal synthesis of (-)-colletol is described using as the key steps Jacobsen's kinetic resolution and a Sharpless asymmetric epoxidation. The synthesis of tarchonanthuslactone and the seco acid proceeded in 14% and 13% overall yield, respectively, starting from chiral (R)-propylene oxide.
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