English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Total synthesis of 9-dihydroerythronolide B derivatives and of erythronolide B

Mulzer, J., Kirstein, H. M., Buschmann, J., Lehmann, C. W., & Luger, P. (1991). Total synthesis of 9-dihydroerythronolide B derivatives and of erythronolide B. Journal of the American Chemical Society, 113(3), 910-923. doi:10.1021/ja00003a026.

Item is

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Mulzer, Johann1, Author
Kirstein, Holger M.1, Author
Buschmann, Jürgen2, Author
Lehmann, Christian W.2, Author              
Luger, Peter2, Author
Affiliations:
1Institut für Organische Chemie, Freie Universität Berlin, Takustr. 3, D-1000 Berlin 33, ou_persistent22              
2Institut für Kristallographie, Freie Universität Berlin, Takustr. 6, D-1000 Berlin 33, West Germany, ou_persistent22              

Content

show
hide
Free keywords: -
 Abstract: A convergent total synthesis (22 steps on the longest linear route) of (-)-erythronolide B (5) and two 9-dihydro derivatives (52 and 54) thereof from (R)-2,3-O-isopropylideneglyceraldehyde (20) as the only source of chirality is described. A key step of the synthesis is the regio- and stereocontrolled coupling of the allyl sulfide anion 39 and ketone 26, which can be directed to either α-adduct 40 or 41 by an appropriate choice of the conditions (Scheme V, Table II). From 40 and 41 the seco acids 47 and 49 are prepared, which are smoothly macrolactonized to 50 and 51 according to a modified Yamaguchi procedure. Hydroboration of 50 and 51 proceeds under macrocyclic stereocontrol to afford the 9-dihydroerythronolide B derivatives 52 and 54, of which 54 is converted into 5 by a known oxidation-deketalizaton sequence.

Details

show
hide
Language(s): eng - English
 Dates: 1990-04-091991-01-01
 Publication Status: Published in print
 Pages: 14
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja00003a026
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 113 (3) Sequence Number: - Start / End Page: 910 - 923 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870