Synlett 2006(1): 0061-0064  
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

Young-Ju Kim, Jinsung Tae*
Department of Chemistry and Center for Bioactive Molecular Hybrids (CBMH), Yonsei University, Seoul 120-749, Korea
Fax: +82(2)3647050; e-Mail: jstae@yonsei.ac.kr;
Further Information

Publication History

Received 21 September 2005
Publication Date:
16 December 2005 (online)

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.

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.