A versatile, non-biomimetic route to the preussomerins: syntheses of (+/-)-preussomerins F, K and L

E  Quesada; M  Stockley; J P  Ragot; M E  Prime; A C  Whitwood; R J K  Taylor

doi:10.1039/b407895k

A versatile, non-biomimetic route to the preussomerins: syntheses of (+/-)-preussomerins F, K and L

E Quesada, M Stockley, J P Ragot, M E Prime, A C Whitwood, R J K Taylor

Chemistry

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

Abstract

The first total syntheses of the title fungal metabolites preussomerins F, K and L are described and their structures confirmed thereby. The syntheses were achieved following a versatile, unified, non-biomimetic approach, which is easily extendable to prepare other known and novel members of this family. Key steps include the functionalisation of a 2-arylacetal anion, tandem one-pot Friedel-Crafts cyclisation-deprotection, regioselective substrate-directable hydrogenation and reductive-opening of epoxides.

Original language	English
Pages (from-to)	2483-2495
Number of pages	13
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	17
DOIs	https://doi.org/10.1039/b407895k
Publication status	Published - 2004

Keywords

BIOLOGICALLY-ACTIVE METABOLITES
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
CRYSTAL-STRUCTURE ANALYSIS
FUNGUS PREUSSIA-ISOMERA
SILYL ENOL ETHERS
STRUCTURE ELUCIDATION
FARNESYLTRANSFERASE INHIBITORS
ANTIFUNGAL METABOLITES
ABSOLUTE-CONFIGURATION
CONIOTHYRIUM-PALMARUM

Access to Document

10.1039/b407895k

http://dx.doi.org/10.1039/b407895k

Cite this

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title = "A versatile, non-biomimetic route to the preussomerins: syntheses of (+/-)-preussomerins F, K and L",

abstract = "The first total syntheses of the title fungal metabolites preussomerins F, K and L are described and their structures confirmed thereby. The syntheses were achieved following a versatile, unified, non-biomimetic approach, which is easily extendable to prepare other known and novel members of this family. Key steps include the functionalisation of a 2-arylacetal anion, tandem one-pot Friedel-Crafts cyclisation-deprotection, regioselective substrate-directable hydrogenation and reductive-opening of epoxides.",

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author = "E Quesada and M Stockley and Ragot, {J P} and Prime, {M E} and Whitwood, {A C} and Taylor, {R J K}",

year = "2004",

doi = "10.1039/b407895k",

language = "English",

volume = "2",

pages = "2483--2495",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "The Royal Society of Chemistry",

number = "17",

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TY - JOUR

T1 - A versatile, non-biomimetic route to the preussomerins: syntheses of (+/-)-preussomerins F, K and L

AU - Quesada, E

AU - Stockley, M

AU - Ragot, J P

AU - Prime, M E

AU - Whitwood, A C

AU - Taylor, R J K

PY - 2004

Y1 - 2004

N2 - The first total syntheses of the title fungal metabolites preussomerins F, K and L are described and their structures confirmed thereby. The syntheses were achieved following a versatile, unified, non-biomimetic approach, which is easily extendable to prepare other known and novel members of this family. Key steps include the functionalisation of a 2-arylacetal anion, tandem one-pot Friedel-Crafts cyclisation-deprotection, regioselective substrate-directable hydrogenation and reductive-opening of epoxides.

AB - The first total syntheses of the title fungal metabolites preussomerins F, K and L are described and their structures confirmed thereby. The syntheses were achieved following a versatile, unified, non-biomimetic approach, which is easily extendable to prepare other known and novel members of this family. Key steps include the functionalisation of a 2-arylacetal anion, tandem one-pot Friedel-Crafts cyclisation-deprotection, regioselective substrate-directable hydrogenation and reductive-opening of epoxides.

KW - BIOLOGICALLY-ACTIVE METABOLITES

KW - ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS

KW - CRYSTAL-STRUCTURE ANALYSIS

KW - FUNGUS PREUSSIA-ISOMERA

KW - SILYL ENOL ETHERS

KW - STRUCTURE ELUCIDATION

KW - FARNESYLTRANSFERASE INHIBITORS

KW - ANTIFUNGAL METABOLITES

KW - ABSOLUTE-CONFIGURATION

KW - CONIOTHYRIUM-PALMARUM

U2 - 10.1039/b407895k

DO - 10.1039/b407895k

M3 - Article

SN - 1477-0520

VL - 2

SP - 2483

EP - 2495

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 17

ER -