Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone

Michael J Robertson-Ralph; Sean Ng; Kevin I Booker-Milburn

doi:10.1021/acs.orglett.6b00067

Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone

Michael J Robertson-Ralph, Sean Ng, Kevin I Booker-Milburn

School of Chemistry

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Abstract

A photochemical approach to the cytotoxic lactone (+)-goniofufurone (1) is reported. Paterno−̀ Büchi [2 + 2] photo- cycloaddition from known enol ether 4, derived from the readily available sugar D-isosorbide, yielded oxetane 7. This slow, dilute reaction was scaled up by using flow photochemistry to yield >40 g of 7. Installation of the key lactone ring was achieved via a unique Wacker- style oxidation of an enol−ether bond. Acid-catalyzed aqueous ring opening provided 1 in five steps from 4 (11.5% overall).

Original language	English
Pages (from-to)	968-971
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	5
Early online date	18 Feb 2016
DOIs	https://doi.org/10.1021/acs.orglett.6b00067
Publication status	Published - 4 Mar 2016

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b00067. Please refer to any applicable terms of use of the publisher.
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Factory in a Fumehood.
Booker-Milburn, K. I. (Principal Investigator)
1/10/13 → 1/03/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

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title = "Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone",

abstract = "A photochemical approach to the cytotoxic lactone (+)-goniofufurone (1) is reported. Paterno{\`−} B{\"u}chi [2 + 2] photo- cycloaddition from known enol ether 4, derived from the readily available sugar D-isosorbide, yielded oxetane 7. This slow, dilute reaction was scaled up by using flow photochemistry to yield >40 g of 7. Installation of the key lactone ring was achieved via a unique Wacker- style oxidation of an enol−ether bond. Acid-catalyzed aqueous ring opening provided 1 in five steps from 4 (11.5% overall).",

author = "Robertson-Ralph, {Michael J} and Sean Ng and Booker-Milburn, {Kevin I}",

year = "2016",

month = mar,

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doi = "10.1021/acs.orglett.6b00067",

language = "English",

volume = "18",

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journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone

AU - Robertson-Ralph, Michael J

AU - Ng, Sean

AU - Booker-Milburn, Kevin I

PY - 2016/3/4

Y1 - 2016/3/4

N2 - A photochemical approach to the cytotoxic lactone (+)-goniofufurone (1) is reported. Paterno−̀ Büchi [2 + 2] photo- cycloaddition from known enol ether 4, derived from the readily available sugar D-isosorbide, yielded oxetane 7. This slow, dilute reaction was scaled up by using flow photochemistry to yield >40 g of 7. Installation of the key lactone ring was achieved via a unique Wacker- style oxidation of an enol−ether bond. Acid-catalyzed aqueous ring opening provided 1 in five steps from 4 (11.5% overall).

AB - A photochemical approach to the cytotoxic lactone (+)-goniofufurone (1) is reported. Paterno−̀ Büchi [2 + 2] photo- cycloaddition from known enol ether 4, derived from the readily available sugar D-isosorbide, yielded oxetane 7. This slow, dilute reaction was scaled up by using flow photochemistry to yield >40 g of 7. Installation of the key lactone ring was achieved via a unique Wacker- style oxidation of an enol−ether bond. Acid-catalyzed aqueous ring opening provided 1 in five steps from 4 (11.5% overall).

U2 - 10.1021/acs.orglett.6b00067

DO - 10.1021/acs.orglett.6b00067

M3 - Article (Academic Journal)

C2 - 26890072

SN - 1523-7060

VL - 18

SP - 968

EP - 971

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone

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Factory in a Fumehood.

3-month Core Capability for Chemistry Research

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