Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach

Toru Motozaki, Kiyoto Sawamura, Akari Suzuki, Keigo Yoshida, Tatsuo Ueki, Aiko Ohara, Ryosuke Munakata, Kenichi Takao, Kin Ichi Tadano

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Abstract

(Chemical Equation Presented) Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and π-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the β-carbon, which in turn was prepared from a known allylated malic acid derivative.

Original languageEnglish
Pages (from-to)2261-2264
Number of pages4
JournalOrganic Letters
Volume7
Issue number11
DOIs
Publication statusPublished - 2005 May 26

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ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Motozaki, T., Sawamura, K., Suzuki, A., Yoshida, K., Ueki, T., Ohara, A., Munakata, R., Takao, K., & Tadano, K. I. (2005). Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach. Organic Letters, 7(11), 2261-2264. https://doi.org/10.1021/ol0507625