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

Access to Document

10.1002/anie.201409818

Cite this

@article{2bcc0062c1294d4894196088a0b2cf89,

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.}",

note = "Publisher Copyright: {\textcopyright} 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = feb,

day = "9",

doi = "10.1002/anie.201409818",

language = "English",

volume = "54",

pages = "1795--1798",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "6",

}

TY - JOUR

T1 - Total synthesis of ramonanins A-D

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

Y1 - 2015/2/9

N2 - 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.

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

KW - Natural products

UR - http://www.scopus.com/inward/record.url?scp=84922032540&partnerID=8YFLogxK

U2 - 10.1002/anie.201409818

DO - 10.1002/anie.201409818

M3 - Article

SN - 1433-7851

VL - 54

SP - 1795

EP - 1798

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Total synthesis of ramonanins A-D

Abstract

Access to Document

Other files and links

Fingerprint

Cite this