Tetrahedron Letters p. 4861 - 4862 (1999)
Update date:2022-08-05
Topics: Asymmetric synthesis Synthetic route γ-lactones δ-lactones
Couladourosand, Elias A.
Mihou, Anastasia P.
Five (or six) membered asymmetric lactones are synthesized from γ- butyrolactone (or δ-valerolactone) in a straightforward way using the following reaction sequence: reduction, Wittig-Schlosser coupling, Sharpless asymmetric dihydroxylation, oxidation and lactonization. Thus, (-)muricatacin is synthesized in six steps (43% overall yield). Furthermore, (5R,6S)-6- acetoxy-hexadecanolide is prepared in eight steps (38% overall yield) via a carbonate ester, utilizing a novel lactonization with inversion of stereochemistry.
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