@article{a07bb96a3af64e54890afbb976e6f30e,
title = "Formal synthesis of tubelactomicins via a transannular Diels-Alder approach",
abstract = "A formal synthesis of the antimicrobial tricyclic macrolides, tubelactomicins A and E, featured by a transannular Diels-Alder (TADA) approach, has been explored. The key issue for the transannular cyclization was the synthesis of a 24-membered macrolactone equipped with all the requisite functionalities, which has been achieved using an intramolecular Hiyama cross-coupling strategy. The Hiyama coupling reaction spontaneously triggered off the TADA reaction. From the endo-TADA adduct, formal syntheses of tubelactomicins A and E were achieved. The 24-membered macrolactone formation was also achieved via an intramolecular ring-closing metathesis approach.",
keywords = "Hiyama coupling, Macrolide antibiotics, Ring-closing olefin metathesis, Transannular Diels-Alder reaction, Tubelactomicins",
author = "Toshimi Anzo and Akari Suzuki and Kiyoto Sawamura and Toru Motozaki and Madoka Hatta and Takao, {Ken ichi} and Tadano, {Kin ichi}",
note = "Funding Information: We thank Dr. Masayuki Igarashi (the Institute of Microbial Chemistry) for providing us the samples and spectral copies ( 1 H and 13 C NMR, IR) of tubelactomicins. This work was supported by Grants-in-Aid for Scientific Research on Priority Areas (A) {\textquoteleft}Creation of Biologically Functional Molecules (18032069){\textquoteright}. ",
year = "2007",
month = nov,
day = "26",
doi = "10.1016/j.tetlet.2007.10.002",
language = "English",
volume = "48",
pages = "8442--8448",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "48",
}