107941-49-1Relevant academic research and scientific papers
The first total synthesis of lactonamycin, a hexacyclic antitumor antibiotic
Tatsuta, Kuniaki,Tanaka, Hiroaki,Tsukagoshi, Hitomi,Kashima, Takafumi,Hosokawa, Seijiro
scheme or table, p. 5546 - 5549 (2010/11/03)
The total synthesis of lactonamycin has been achieved. The synthesis includes sequential intramolecular conjugate addition of alcohols to the acetylenic ester, stereoselective glycosylation of the tertiary alcohol, and Michael-Dieckmann type cyclization w
Synthetic Approach to Aklavinone Using 2-Oxo-2H-pyran-5-carboxylate (Coumalate) Intermediates
Jung, Michael E.,Hagenah, Jeffrey A.
, p. 1889 - 1902 (2007/10/02)
A novel approach for the preparation of aklavinone 5 is described in which the key step is the cycloaddition of a substituted coumalate with a ketene acetal to produce a masked A ring with the C and D rings attached.The 4-(arylmethyl)coumalate 53 was prepared from naphthalene-1,5-diol (6) by a seven step route involving as the key step the cyclocondensation of the methyl (arylmethyl)propiolate 52 with methyl 3-oxopentanoate 10.Cycloaddition of 53 with dimethyl ketene acetal 12 produced the potential A-ring precursor 67, which could not be cleanly reduced, thereby ending this scheme.The preparation of functionalized 4,6-dialkylpyrone-5-carboxylates and their use in the synthesis of bicyclic lactones and substituted benzoates via cycloaddition reactions are also described.
PREPARATION AND CYCLOADDITION OF FUNCTIONALIZED 4,6-DIALKYLPYRONE-5-CARBOXYLATES. SYNTHESIS OF BICYCLIC LACTONES AND SUBSTITUTED BENZOATES
Jung, Michael E.,Hagenah, Jeffrey A.
, p. 117 - 121 (2007/10/02)
Several alkyl pyrone-5-carboxylates (coumalates) with alkyl and functionalized alkyl substituents at C4 and C6 have been prepared by a general route; their cycloadditions with electron-rich olefins have been carried out to provide aromatic and non-aromati
