Synthesis of the C1 to C13 tetrahydropyranyl-resorcylate core of paecilomycin B
File(s)
Accepted version
Author(s)
Cookson, Rosa
White, Andrew JP
Barrett, Anthony GM
Type
Journal Article
Abstract
A d-Glucose derived tetrahydropyran was converted into the C1 to C13 tetrahydropyranyl-resorcylate core of paecilomycin B in seven steps. Key transformations included the synthesis of a diketo-ester dioxinone, which upon thermolysis underwent a retro-hetero-Diels-Alder fragmentation to generate an acyl ketene. This was subsequently trapped by a secondary alcohol affording a triketo-ester, which was efficiently aromatized to produce the advanced resorcylate intermediate.
Date Issued
2018-09-20
Date Acceptance
2018-05-29
Citation
TETRAHEDRON, 2018, 74 (38), pp.5040-5048
ISSN
0040-4020
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Start Page
5040
End Page
5048
Journal / Book Title
TETRAHEDRON
Volume
74
Issue
38
Copyright Statement
© 2018 Elsevier Ltd. All rights reserved. This manuscript is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/
Sponsor
Commission of the European Communities
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000445305400014&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Grant Number
267281
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
Biomimetic synthesis
Resorcylic acid lactone
Retro-Diels-Alder
Ketene
Macrocycle
LACTONES
Publication Status
Published
Date Publish Online
2018-06-05