Synthetic strategies of marine polycyclic ethers via intramolecular allylations: Linear and convergent approaches

Isao Kadota; Yoshinori Yamamoto

doi:10.1021/ar040118a

Synthetic strategies of marine polycyclic ethers via intramolecular allylations: Linear and convergent approaches

Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journal › Article › peer-review

74 Citations (Scopus)

Abstract

Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of α-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).

Original language	English
Pages (from-to)	423-432
Number of pages	10
Journal	Accounts of chemical research
Volume	38
Issue number	5
DOIs	https://doi.org/10.1021/ar040118a
Publication status	Published - May 1 2005
Externally published	Yes

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Chemistry(all)

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This output contributes to the following Sustainable Development Goal(s)

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10.1021/ar040118a

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abstract = "Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of α-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).",

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N2 - Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of α-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).

AB - Strategies for the synthesis of polycyclic ethers based on intramolecular allylations are overviewed. The intramolecular condensation of allylic stannanes and aldehydes is a powerful tool for the synthesis of oxepane derivatives. The reaction is successfully applied to the iterative total synthesis of hemibrevetoxin B (2). Further, the intramolecular allylation of α-acetoxy ethers provides an efficient method for the convergent synthesis of polycyclic ethers. The usefulness of the latter strategy is demonstrated in the convergent total synthesis of gambierol (4).

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Synthetic strategies of marine polycyclic ethers via intramolecular allylations: Linear and convergent approaches

Abstract

ASJC Scopus subject areas

UN SDGs

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