Total synthesis of ramonanins A-D

Ross S. Harvey; Emily G. Mackay; Lukas Roger; Michael N. Paddon-Row; Michael S. Sherburn; Andrew L. Lawrence

doi:10.1002/anie.201409818

Total synthesis of ramonanins A-D

Ross S. Harvey, Emily G. Mackay, Lukas Roger, Michael N. Paddon-Row, Michael S. Sherburn, Andrew L. Lawrence

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

21 Citations (Scopus)

Abstract

The first total synthesis of the ramonanin family of lignan natural products is described. The short synthesis involves a 2,5-diaryl-3,4-dimethylene tetrahydrofuran intermediate, which participates in an unexpectedly facile Diels-Alder dimerization, generating all four natural products. Insights into the reactivity and stereoselectivity of the key dimerization are provided through computational studies employing B3LYP/6-31G(d) and M06-2X/6-31G(d) model chemistries.

Original language	English
Pages (from-to)	1795-1798
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	6
DOIs	https://doi.org/10.1002/anie.201409818
Publication status	Published - 9 Feb 2015

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title = "Total synthesis of ramonanins A-D",

abstract = "The first total synthesis of the ramonanin family of lignan natural products is described. The short synthesis involves a 2,5-diaryl-3,4-dimethylene tetrahydrofuran intermediate, which participates in an unexpectedly facile Diels-Alder dimerization, generating all four natural products. Insights into the reactivity and stereoselectivity of the key dimerization are provided through computational studies employing B3LYP/6-31G(d) and M06-2X/6-31G(d) model chemistries.",

keywords = "Biomimetic synthesis, Diels-Alder reactions, Enyne metathesis, Lignans, Natural products",

author = "Harvey, \{Ross S.\} and Mackay, \{Emily G.\} and Lukas Roger and Paddon-Row, \{Michael N.\} and Sherburn, \{Michael S.\} and Lawrence, \{Andrew L.\}",

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AU - Harvey, Ross S.

AU - Mackay, Emily G.

AU - Roger, Lukas

AU - Paddon-Row, Michael N.

AU - Sherburn, Michael S.

AU - Lawrence, Andrew L.

PY - 2015/2/9

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AB - The first total synthesis of the ramonanin family of lignan natural products is described. The short synthesis involves a 2,5-diaryl-3,4-dimethylene tetrahydrofuran intermediate, which participates in an unexpectedly facile Diels-Alder dimerization, generating all four natural products. Insights into the reactivity and stereoselectivity of the key dimerization are provided through computational studies employing B3LYP/6-31G(d) and M06-2X/6-31G(d) model chemistries.

KW - Biomimetic synthesis

KW - Diels-Alder reactions

KW - Enyne metathesis

KW - Lignans

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Total synthesis of ramonanins A-D

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