Total synthesis of nostodione A, a cyanobacterial metabolite.
نویسندگان
چکیده
The first total synthesis of the mitotic spindle poison nostodione A is described. The inherent oxidative sensitivity of indoles is utilized for a late introduction of a second carbonyl to the cyclopent[b]indole-2-one system. The tricyclic system is prepared from indole-3-acetic acid and O-silylated 4-ethynylphenol, using a stereoselective intramolecular reductive Heck cyclization as the key transformation.
منابع مشابه
Total synthesis of the cyanobacterial metabolite nostodione A: discovery of its antiparasitic activity against Toxoplasma gondii.
A total synthesis of the cyanobacterial natural product nostodione A is reported involving a convergent, diversity-oriented route. A small assemblage of structural analogues were prepared and their cytotoxicity and anti-invasion activity against the protozoal parasite Toxoplasma gondii is reported for the first time.
متن کاملSynthesis of the cyanobacterial metabolite nostodione A, structural studies and potent antiparasitic activity against Toxoplasma gondii.
A total synthesis of the cyanobacterial natural product nostodione A is reported involving a convergent, diversity-oriented route, enabling the assembly of a mini-library of structural analogues. The first single crystal X-ray structural determination on a member of this series is reported along with SAR studies identifying potent inhibitors of invasion and replication of the parasitic protozoa...
متن کاملThe cyanobacterial pigments scytonemin and nostodione A Synthesis, photophysicochemical behavior and biological studies
The natural UV-screener scytonemin is found in a plethora of cyanobacterial species. Its UVprotective ability allows the bacteria to thrive in inhospitable locations exposed to intense solar radiation. Scytonemin has a dimeric structure consisting of two 1-1' linked 3-(4hydroxybenzylidene)cyclopenta[b]indole-2-one moieties. The cyanobacterial pigment nostodione A consists of the same skeleton, ...
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Total synthesis of the cyanobacterial metabolite largamide B and the disproval of its originally assigned stereochemistry as well as confirmation of the revised stereochemistry are reported.
متن کاملNostodione A, a Novel Mitotic Spindle Poison* from a Blue-Green Alga Nostoc commune
Akio Kobayashi, Shin-ichiro Kajiyama, Kunifumi Inawaka, Hiroshi Kanzaki and Kazuyoshi Kawazu Department of Agricultural Science, Faculty of Agriculture, Okayama University, Okayama 700. Japan Z. Naturforsch. 49c, 464-470 (1994); received February 4, 1994 Nostodione A, Mitotic Spindle Poison. Blue-Green Alga, Nostoc commune, Sea-Urchin Eggs A novel antimitotic compound named Nostodione A (Nd A) ...
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ورودعنوان ژورنال:
- Organic letters
دوره 14 24 شماره
صفحات -
تاریخ انتشار 2012