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Synlett 2006(1): 0061-0064
DOI: 10.1055/s-2005-922774
DOI: 10.1055/s-2005-922774
LETTER
© Georg Thieme Verlag Stuttgart · New York
Resolution of 2-Silyloxy-1-oxiranyl-4-pentenes by HKR: Total Synthesis of (5S,7R)-Kurzilactone
Weitere Informationen
Received
21 September 2005
Publikationsdatum:
16. Dezember 2005 (online)
Publikationsverlauf
Publikationsdatum:
16. Dezember 2005 (online)
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Abstract
Enantiomerically pure syn- and anti-2-silyloxy-1-oxiranyl-4-pentenes were prepared by using Jacobsen’s hydrolytic kinetic resolution (HKR) method. A resolved epoxypentenol generated in this fashion was used in the total synthesis of (5S,7R)-kurzilactone by a pathway employing epoxide ring-opening and RCM reactions in key steps.
Key words
epoxides - hydrolytic kinetic resolution - kurzilactone - metathesis - total synthesis
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References and Notes
The ee (%) of the resolved epoxides and diols were determined by HPLC using the Chiralpak-OD-H column after conversion to the corresponding para-nitrobenzoates by Mitsunobu inversion reactions.
16The preference of the syn-epoxide (±)-10 over the anti-epoxide (±)-13 in the HKR reaction is not clear at this point.