Synlett 2020; 31(05): 421-433
DOI: 10.1055/s-0039-1691580
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© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Natural Products Using Intramolecular Nozaki–Hiyama–Takai–Kishi Reactions

,
Akihiro Ogura
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan   eMail: takao@applc.keio.ac.jp
,
Keisuke Yoshida
,
Siro Simizu
› Institutsangaben
This work was supported by the MEXT-Supported Program for the Strategic Research Foundation at Private Universities, 2012–2016, Japan Society for the Promotion of Science (JSPS), Grants-in-Aid for Scientific Research (KAKENHI) (Grant Nos. 15750094 and 15K05504) from Japan Society for the Promotion of Science (JSPS), the Naito Foundation, and the Keio Gijuku Academic Development Funds.
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Publikationsverlauf

Received: 08. Dezember 2019

Accepted after revision: 29. Dezember 2019

Publikationsdatum:
03. Februar 2020 (online)


Abstract

In this Account, we describe our studies on the total synthesis of several natural products using intramolecular Nozaki–Hiyama–Takai–Kishi (NHTK) reactions. In each synthesis, an NHTK reaction is used to efficiently construct a medium-sized ring. These examples demonstrate the utility of the intramolecular NHTK reaction in natural product synthesis.

1 Introduction

2 Total Synthesis of (+)-Pestalotiopsin A

3 Total Synthesis of (+)-Cytosporolide A

4 Total Synthesis of (+)-Vibsanin A

5 Total Syntheses of (+)-Aquatolide and Related Humulanolides

6 Conclusion