Concise Total Synthesis of Tronocarpine

• Nakayama, Atsushi

• Nakamura, Tenta

• Zaima, Toshihiro

• Fujimoto, Saho

• Karanjit, Sangita

• Namba, Kosuke

抄録

A concise total synthesis of tronocarpine, a chippiine-type indole alkaloid, was accomplished. The key feature of this total synthesis is a one-pot construction of the pentacyclic skeleton containing an azabicyclo[3.3.1]nonane core by tandem cyclization from an indole derivative having all carbon side chains and functional groups. This tandem cyclization consists of α,β-unsaturated aldehyde formation, intramolecular aldol reaction, six-membered lactamization, azide reduction, and seven-membered lactamization. The stereochemical outcome in this tandem cyclization is controlled by the stereocenter at the C14 position. This strategy can be utilized to synthesize other chippiine-type alkaloids with azabicyclo[3.3.1]nonane skeletons.

収録刊行物

• Angewandte Chemie International Edition

  Angewandte Chemie International Edition 60 (2), 635-639, 2020-09-24

  Wiley-VCH|German Chemical Society

キーワード

• total synthesis
• natural product
• tandem cyclization
• equilibrium
• alkaloid

詳細情報

• CRID: 1050008597643729280
• NII論文ID: 120007168797
• NII書誌ID: AA0052535X
• ISSN: 14337851
• ISSN: 15213773
• DOI: 10.1002/anie.202009966
• Web Site: http://repo.lib.tokushima-u.ac.jp/116180
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202009966
• Web Site: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.202009966
• 本文言語コード: en
• 資料種別: journal article
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