Resolution of 2-Silyloxy-1-oxiranyl-4-pentenes by HKR: Total Synthesis of (5S,7R)-Kurzilactone

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

References and Notes

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15

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.

16

The preference of the syn-epoxide (±)-10 over the anti-epoxide (±)-13 in the HKR reaction is not clear at this point.