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Asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001.
J Org Chem
January 2009
Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
trans-4-Hydroxy-L-proline was converted into a tricyclic compound representing three contiguous rings of the anticancer antibiotic MPC1001. The tricyclic model contains the dihydrooxepin and diketopiperazine subunits, as well as one of the sulfur atoms of the natural product. The diketopiperazine unit was formed by a new method that involves cyclization of an enolate onto the carbonyl of a phenyl carbamate, and the dihydrooxepin ring was generated by using an acid-induced cyclization of an alcohol onto the beta-carbon of a vinylogous amide.
View Article and Find Full Text PDFSynthesis of dihydrooxepin models related to the antitumor antibiotic MPC1001.
Org Lett
July 2007
Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
4-Hydroxy-L-proline was converted into the tetrahydrooxepino[4,3-b]pyrrole ring system characteristic of the potent antitumor agent MPC1001. Key steps were regioselective formation of a vinylogous amide by use of Bredereck's reagent and acid-induced cyclization of an alcohol onto the carbon-carbon double bond of that amide by addition-elimination to generate the seven-membered oxacyclic subunit.
View Article and Find Full Text PDFMPC1001, a new antitumor antibiotic produced by Cladorrhinum sp.
J Antibiot (Tokyo)
August 2004
Tokyo Research Laboratories, Kyowa Hakko Kogyo Co., Ltd., 3-6-6 Asahimachi, Machida-shi, Tokyo 194-8533, Japan.
MPC1001 and its analogues: new antitumor agents from the fungus Cladorrhinum species.
Org Lett
October 2004
Tokyo Research Laboratories, Kyowa Hakko Kogyo Co., Ltd., 3-6-6 Asahimachi, Machida, Tokyo 194-8533, Japan.
[structure: see text] Eight new compounds, MPC1001 and MPC1001B-H, were isolated from the fungus Cladorrhinum sp. KY4922. Multiple NMR experiments and CD data revealed MPC1001 to be an O-methyl derivative of emestrin, a 15-membered antifungal antibiotic containing a unique epidithiodioxopiperazine skeleton.
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