@article{ac7047bb42884f22b7d37bf0088d5484,
title = "Total synthesis of JBIR-03 and asporyzin C",
abstract = "The first enantioselective total synthesis of JBIR-03 and asporyzin C, indole diterpenoids of fungal origin exhibiting a range of pharmacologically important biological activities, has been accomplished from a known bicyclic keto alcohol in 13 and 14 steps, respectively. A hydroxy-directed cyclopropanation and Pd(II)-mediated indole ring formation were exploited as the key steps to obtain a pivotal pentacylic intermediate, which was converted into asporyzin C via chain elongation using cross-metathesis and then into JBIR-03 by Pd(II)-catalyzed tetrahydrofuran ring formation in an exclusively diastereoselective manner.",
keywords = "Asporyzin, Indole diterpenoid, JBIR-03, Palladium catalysis, Total synthesis",
author = "Tetsuro Murokawa and Masaru Enomoto and Takaaki Teranishi and Yusuke Ogura and Shigefumi Kuwahara",
note = "Funding Information: This work was financially supported by the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED). We are grateful to Drs. Kazuo Shin-ya and Takuya Hashimoto (AIST) for providing the NMR spectra of natural JBIR-03. Thanks are also due to Ms. Yuka Taguchi (Tohoku University) for her help with NMR and MS measurements. Funding Information: This work was financially supported by the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED). We are grateful to Drs. Kazuo Shin-ya and Takuya Hashimoto (AIST) for providing the NMR spectra of natural JBIR-03. Thanks are also due to Ms. Yuka Taguchi (Tohoku University) for her help with NMR and MS measurements.",
year = "2018",
month = nov,
day = "14",
doi = "10.1016/j.tetlet.2018.10.009",
language = "English",
volume = "59",
pages = "4107--4109",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "46",
}