Total Synthesis of Naphterpin and Marinone Natural Products

Lauren A.M. Murray; Thomas Fallon; Christopher J. Sumby; Jonathan H. George

doi:10.1021/acs.orglett.9b03095

Total Synthesis of Naphterpin and Marinone Natural Products

Lauren A.M. Murray
, Thomas Fallon
, Christopher J. Sumby
, Jonathan H. George

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

28 Citations (Scopus)

Abstract

A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6Ï€-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.

Original language	English
Pages (from-to)	8312-8315
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.9b03095
Publication status	Published - 18 Oct 2019
Externally published	Yes

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10.1021/acs.orglett.9b03095

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title = "Total Synthesis of Naphterpin and Marinone Natural Products",

abstract = "A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6{\"I}€-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.",

author = "Murray, \{Lauren A.M.\} and Thomas Fallon and Sumby, \{Christopher J.\} and George, \{Jonathan H.\}",

note = "Funding Information: This work was supported by an Australian Research Council Future Fellowship awarded to J.H.G. (FT170100437). Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b03095",

language = "English",

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AU - Murray, Lauren A.M.

AU - Fallon, Thomas

AU - Sumby, Christopher J.

AU - George, Jonathan H.

PY - 2019/10/18

Y1 - 2019/10/18

N2 - A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6Ï€-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.

AB - A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6Ï€-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.

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DO - 10.1021/acs.orglett.9b03095

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SN - 1523-7060

VL - 21

SP - 8312

EP - 8315

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Total Synthesis of Naphterpin and Marinone Natural Products

Abstract

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