SYNTHESIS OF C1–C6 FRAGMENT FOR EPOTHILONE A VIA LIPASE-CATALYZED OPTICAL RESOLUTION

Kosei Shioji Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka, 814-0180, Japan

Hitomi Kawaoka Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka, 814-0180, Japan

Asami Miura Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka, 814-0180, Japan

Kentaro Okuma Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka, 814-0180, Japan

Abstract

Synthesis of 5-oxo-(3S)-hydroxy-4,4-dimethylheptanoic acid (1), C1–C6 fragment of epothilone A, is described. Racemic tert-butyl 5-oxo-(3S)-acetoxy-4,4-dimethylheptanoate (5) was prepared by acylation of enamine followed by aldol condensation. Optical resolution of the heptanoate 5 was carried out by lipase catalyzed hydrolysis (yield 50%, > 98% e.e.).

Acknowledgments

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

SYNTHESIS OF C1–C6 FRAGMENT FOR EPOTHILONE A VIA LIPASE-CATALYZED OPTICAL RESOLUTION

Information for

Open access

Opportunities

Help and information

SYNTHESIS OF C1–C6 FRAGMENT FOR EPOTHILONE A VIA LIPASE-CATALYZED OPTICAL RESOLUTION

Abstract

Acknowledgments

Reprints and Corporate Permissions

Academic Permissions

Related research

To cite this article:

Download citation

Information for

Open access

Opportunities

Help and information

Keep up to date

Your download is now in progress and you may close this window

Login or register to access this feature