English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
Add to Basket
  Local TagsRelease HistoryDetailsSummary

Released
Journal Article

FORMAL TOTAL SYNTHESES OF CROCACIN A-D

MPS-Authors
/persons/resource/persons58427

Besev,  M.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58453

Brehm,  C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58380

Fürstner,  A.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource
No external resources are shared
Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available
Citation

Besev, M., Brehm, C., & Fürstner, A. (2005). FORMAL TOTAL SYNTHESES OF CROCACIN A-D. Collection of Czechoslovak Chemical Communications, 70(10), 1696-1708. doi:10.1135/cccc20051696.


Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-9523-B
Abstract
A concise route to the common polyketide fragment 5 of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features a syn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzed anti-selective addition of propargyl mesylate 10 to the chiral aldehyde 9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.