A short biomimetic synthesis of the meroterpenoids guajadial and psidial A

A.L. Lawrence; R.M. Adlington; J.E. Baldwin; V. Lee; J.A. Kershaw; A.L. Thompson; Andrew Lawrence

doi:10.1021/ol100138k

A short biomimetic synthesis of the meroterpenoids guajadial and psidial A

A.L. Lawrence, R.M. Adlington, J.E. Baldwin, V. Lee, J.A. Kershaw, A.L. Thompson, Andrew Lawrence

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

Abstract

The biosynthesis of the meroterpenoid guajadial was previously hypothesized to occur via a hetero-Diels-Alder reaction between caryophyllene and an o-quinone methide. This hypothesis has been verified via the biomimetic synthesis of guajadial and psidial A in an aqueous three-component coupling reaction, between caryophyllene, benzaldehyde, and diformylphloroglucinol.

Original language	English
Pages (from-to)	1676-1679
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	8
DOIs	https://doi.org/10.1021/ol100138k
Publication status	Published - 16 Apr 2010

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10.1021/ol100138k

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abstract = "The biosynthesis of the meroterpenoid guajadial was previously hypothesized to occur via a hetero-Diels-Alder reaction between caryophyllene and an o-quinone methide. This hypothesis has been verified via the biomimetic synthesis of guajadial and psidial A in an aqueous three-component coupling reaction, between caryophyllene, benzaldehyde, and diformylphloroglucinol.",

author = "A.L. Lawrence and R.M. Adlington and J.E. Baldwin and V. Lee and J.A. Kershaw and A.L. Thompson and Andrew Lawrence",

year = "2010",

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T1 - A short biomimetic synthesis of the meroterpenoids guajadial and psidial A

AU - Lawrence, A.L.

AU - Adlington, R.M.

AU - Baldwin, J.E.

AU - Lee, V.

AU - Kershaw, J.A.

AU - Thompson, A.L.

AU - Lawrence, Andrew

PY - 2010/4/16

Y1 - 2010/4/16

N2 - The biosynthesis of the meroterpenoid guajadial was previously hypothesized to occur via a hetero-Diels-Alder reaction between caryophyllene and an o-quinone methide. This hypothesis has been verified via the biomimetic synthesis of guajadial and psidial A in an aqueous three-component coupling reaction, between caryophyllene, benzaldehyde, and diformylphloroglucinol.

AB - The biosynthesis of the meroterpenoid guajadial was previously hypothesized to occur via a hetero-Diels-Alder reaction between caryophyllene and an o-quinone methide. This hypothesis has been verified via the biomimetic synthesis of guajadial and psidial A in an aqueous three-component coupling reaction, between caryophyllene, benzaldehyde, and diformylphloroglucinol.

UR - https://www.scopus.com/pages/publications/77951201347

U2 - 10.1021/ol100138k

DO - 10.1021/ol100138k

M3 - Article

AN - SCOPUS:77951201347

SN - 1523-7060

VL - 12

SP - 1676

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JO - Organic letters

JF - Organic letters

IS - 8

ER -

A short biomimetic synthesis of the meroterpenoids guajadial and psidial A

Abstract

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