Synthesis of (±)-Panduratin A and Related Natural Products Using the High Pressure Diels–Alder Reaction

Luke A. Pasfield; Laura de la Cruz; Junming Ho; Michelle L. Coote; Gottfried Otting; Malcolm D. Mcleod

doi:10.1002/ajoc.201200171

Synthesis of (±)-Panduratin A and Related Natural Products Using the High Pressure Diels–Alder Reaction

Luke A. Pasfield, Laura de la Cruz, Junming Ho, Michelle L. Coote, Gottfried Otting, Malcolm D. Mcleod

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

15 Citations (Scopus)

Abstract

Under pressure: PanduratinA (1) has been synthesized in six steps including a high pressure Diels-Alder reaction. This divergent sequence also allowed the synthesis of 4-hydroxypanduratinA, panduratinH, panduratinI, nicolaioidesinB, and 2-hydroxyisopanduratinA. The binding of panduratinA to the dengue virus NS2B-NS3 protease was investigated by NMR spectroscopy.

Original language	English
Pages (from-to)	60-63
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	2
Issue number	1
DOIs	https://doi.org/10.1002/ajoc.201200171
Publication status	Published - Jan 2013
Externally published	Yes

Keywords

Dengue virus
High-pressure chemistry
Natural products
Protein NMR
Total synthesis

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title = "Synthesis of (±)-Panduratin A and Related Natural Products Using the High Pressure Diels–Alder Reaction",

abstract = "Under pressure: PanduratinA (1) has been synthesized in six steps including a high pressure Diels-Alder reaction. This divergent sequence also allowed the synthesis of 4-hydroxypanduratinA, panduratinH, panduratinI, nicolaioidesinB, and 2-hydroxyisopanduratinA. The binding of panduratinA to the dengue virus NS2B-NS3 protease was investigated by NMR spectroscopy.",

keywords = "Dengue virus, High-pressure chemistry, Natural products, Protein NMR, Total synthesis",

author = "Pasfield, {Luke A.} and {de la Cruz}, Laura and Junming Ho and Coote, {Michelle L.} and Gottfried Otting and Mcleod, {Malcolm D.}",

year = "2013",

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T1 - Synthesis of (±)-Panduratin A and Related Natural Products Using the High Pressure Diels–Alder Reaction

AU - Pasfield, Luke A.

AU - de la Cruz, Laura

AU - Ho, Junming

AU - Coote, Michelle L.

AU - Otting, Gottfried

AU - Mcleod, Malcolm D.

PY - 2013/1

Y1 - 2013/1

N2 - Under pressure: PanduratinA (1) has been synthesized in six steps including a high pressure Diels-Alder reaction. This divergent sequence also allowed the synthesis of 4-hydroxypanduratinA, panduratinH, panduratinI, nicolaioidesinB, and 2-hydroxyisopanduratinA. The binding of panduratinA to the dengue virus NS2B-NS3 protease was investigated by NMR spectroscopy.

AB - Under pressure: PanduratinA (1) has been synthesized in six steps including a high pressure Diels-Alder reaction. This divergent sequence also allowed the synthesis of 4-hydroxypanduratinA, panduratinH, panduratinI, nicolaioidesinB, and 2-hydroxyisopanduratinA. The binding of panduratinA to the dengue virus NS2B-NS3 protease was investigated by NMR spectroscopy.

KW - Dengue virus

KW - High-pressure chemistry

KW - Natural products

KW - Protein NMR

KW - Total synthesis

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DO - 10.1002/ajoc.201200171

M3 - Article

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JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

IS - 1

ER -

Synthesis of (±)-Panduratin A and Related Natural Products Using the High Pressure Diels–Alder Reaction

Abstract

Keywords

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