Relay cross metathesis for the iterative construction of terpenoids and synthesis of a diterpene benzoate macrolide of biogenetic relevance to the bromophycolides
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Published version
Author(s)
Bahou, Karim
Braddock, David
Meyer, Adam
Savage, G Paul
Type
Journal Article
Abstract
We report a relay cross metathesis (ReXM) reaction for the construction of terpenoids in an iterative protocol. The protocol features the cross metathesis of a relay-actuated Δ6,7-functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-sesquiterpene. Subsequent functional group manipulation allows for the method to be repeated in an iterative fashion. The method is used for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide family of natural products.
Date Issued
2020-04-17
Date Acceptance
2020-03-27
Citation
Organic Letters, 2020, 22 (8), pp.3176-3179
ISSN
1523-7052
Publisher
American Chemical Society
Start Page
3176
End Page
3179
Journal / Book Title
Organic Letters
Volume
22
Issue
8
Copyright Statement
© 2020 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License (https://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
License URL
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Grant Number
EP/P030742/1
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
EFFICIENT
03 Chemical Sciences
Organic Chemistry
Publication Status
Published
Date Publish Online
2020-03-31