In:
European Journal of Organic Chemistry, Wiley, Vol. 2005, No. 12 ( 2005-06), p. 2459-2467
Abstract:
The antibiotic mensacarcin ( 1 ), which contains nine stereogenic centers and two epoxy functionalities, is a novel antitumor agent that was first isolated from the culture broth of Streptomyces sp. Gö C4/4 found in a soil sample next to the northern cafeteria of the University of Göttingen. For the synthesis of 1 and related structurally simplified analogs, aDiels–Alder reaction of O ‐methyljuglone ( 11 ) and the tetrasubstituted 1,3‐butadiene 22 was performed to give the cycloadduct rac ‐ 28 , which was transformed into the epoxides rac‐ 31 and rac‐ 33 . The cytotoxicity of rac‐ 33 is only 53 times lower than the much more complex 1 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2005:12
DOI:
10.1002/ejoc.200400826
Language:
English
Publisher:
Wiley
Publication Date:
2005
detail.hit.zdb_id:
1475010-7
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