Format:
Online-Ressource
ISSN:
1099-0690
Content:
Abstract: We have accomplished the first total synthesis of longimicin D (1), which displays potent cytotoxicity against human pancreatic carcinoma cells. The bis‐THF core bearing congested stereocenters was constructed by our methodology for synthesis of poly‐THF cores, which consists of asymmetric alkynylation with the C4 unit and stereodivergent THF ring formation. Although we had planned to join the C9–C34 bis‐THF core segment 2 and the C1–C8 γ‐lactone segment 3, a model study revealed that the coupling was difficult. We resolved the problem by applying asymmetric alkynylation of bis‐THF aldehyde 24 with functionalized alkyne 19 respresenting the polymethylene chain from the C3 to C12 position. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
In:
volume:2006
In:
number:6
In:
year:2006
In:
pages:1422-1429
In:
extent:8
In:
European journal of organic chemistry, Weinheim : Wiley-VCH Verl., 1998-, 2006, Heft 6 (2006), 1422-1429 (gesamt 8), 1099-0690
Language:
English
DOI:
10.1002/ejoc.200500850
URN:
urn:nbn:de:101:1-2023090906033237640003
URL:
https://doi.org/10.1002/ejoc.200500850
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023090906033237640003
URL:
https://d-nb.info/1301976377/34
URL:
https://doi.org/10.1002/ejoc.200500850
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