Stereoselective Synthesis of Alcohols, L. Stereoselective Synthesis of a C‐15/C‐27 Segment of the Venturicidines - Research portal of Justus Liebig University Giessen:

Journal article

Stereoselective Synthesis of Alcohols, L. Stereoselective Synthesis of a C‐15/C‐27 Segment of the Venturicidines

Authors list: Hoffmann, RW; Rolle, U; Göttlich, R

Publication year: 1996

Pages: 1717-1724

Journal: Liebigs Annalen - recueil

Volume number: 1996

Issue number: 11

ISSN: 0947-3440

DOI Link: https://doi.org/10.1002/jlac.199619961104

Publisher: Wiley-VCH Verlag

Abstract:
Chain extension of an aldehyde by two ''propionate'' units has been attained by stereoselective allylboration with the chiral 1-methylbutenyl boronate 3 to give, e.g., the homoallylic alcohol 6, followed by a regioselective hydroboration/carbonylation procedure to give, e.g., the epimeric aldehydes 8. The latter were converted into the lactols 10, which equilibrated to the desired epimer. The lactols could again be subjected to an allylboration reaction, initiating a second round of the chain extension protocol. This technique has been used to synthesize in 15 steps in the venturicidene C-15/C-27 segment 23, containing 8 stereogenic centers with the proper absolute configuration.

Authors/Editors

- Uni.-Prof. Dr. Richard Göttlich

Citation Styles

Harvard Citation style: Hoffmann, R., Rolle, U. and Göttlich, R. (1996) Stereoselective Synthesis of Alcohols, L. Stereoselective Synthesis of a C‐15/C‐27 Segment of the Venturicidines, Liebigs Annalen - recueil, 1996(11), pp. 1717-1724. https://doi.org/10.1002/jlac.199619961104

APA Citation style: Hoffmann, R., Rolle, U., & Göttlich, R. (1996). Stereoselective Synthesis of Alcohols, L. Stereoselective Synthesis of a C‐15/C‐27 Segment of the Venturicidines. Liebigs Annalen - recueil. 1996(11), 1717-1724. https://doi.org/10.1002/jlac.199619961104