Total synthesis of (+)-tubelactomicin A. 2. Synthesis of the upper-half segment and completion of the total synthesis

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

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

(Chemical Equation Presented) We have completed the total synthesis of natural (+)-tubelactomicin A (1), a 16-membered macrolide antibiotic. This Letter presents a highly efficient synthesis of the upper-half segment (C14-C24) and the completion of the total synthesis featuring a high-yielding Stille coupling for the connection of the upper-half and lower-half segments and Mukaiyama macrolactonization for the construction of the entire structure of 1.

Original languageEnglish
Pages (from-to)2265-2267
Number of pages3
JournalOrganic Letters
Volume7
Issue number11
DOIs
Publication statusPublished - 2005 May 26

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Macrolides
Anti-Bacterial Agents
synthesis
antibiotics
tubelactomicin A

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Motozaki, T., Sawamura, K., Suzuki, A., Yoshida, K., Ueki, T., Ohara, A., ... Tadano, K. I. (2005). Total synthesis of (+)-tubelactomicin A. 2. Synthesis of the upper-half segment and completion of the total synthesis. Organic Letters, 7(11), 2265-2267. https://doi.org/10.1021/ol050763x

Total synthesis of (+)-tubelactomicin A. 2. Synthesis of the upper-half segment and completion of the total synthesis. / Motozaki, Toru; Sawamura, Kiyoto; Suzuki, Akari; Yoshida, Keigo; Ueki, Tatsuo; Ohara, Aiko; Munakata, Ryosuke; Takao, Kenichi; Tadano, Kin Ichi.

In: Organic Letters, Vol. 7, No. 11, 26.05.2005, p. 2265-2267.

Research output: Contribution to journalArticle

Motozaki, T, Sawamura, K, Suzuki, A, Yoshida, K, Ueki, T, Ohara, A, Munakata, R, Takao, K & Tadano, KI 2005, 'Total synthesis of (+)-tubelactomicin A. 2. Synthesis of the upper-half segment and completion of the total synthesis', Organic Letters, vol. 7, no. 11, pp. 2265-2267. https://doi.org/10.1021/ol050763x
Motozaki, Toru ; Sawamura, Kiyoto ; Suzuki, Akari ; Yoshida, Keigo ; Ueki, Tatsuo ; Ohara, Aiko ; Munakata, Ryosuke ; Takao, Kenichi ; Tadano, Kin Ichi. / Total synthesis of (+)-tubelactomicin A. 2. Synthesis of the upper-half segment and completion of the total synthesis. In: Organic Letters. 2005 ; Vol. 7, No. 11. pp. 2265-2267.
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