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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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Title: Relay cross metathesis for the iterative construction of terpenoids and synthesis of a diterpene benzoate macrolide of biogenetic relevance to the bromophycolides
Authors: Bahou, K
Braddock, D
Meyer, A
Savage, GP
Item 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.
Issue Date: 17-Apr-2020
Date of Acceptance: 27-Mar-2020
URI: http://hdl.handle.net/10044/1/79037
DOI: 10.1021/acs.orglett.0c00935
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.
Sponsor/Funder: Engineering & Physical Science Research Council (EPSRC)
Funder's Grant Number: EP/P030742/1
Keywords: Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
EFFICIENT
03 Chemical Sciences
Organic Chemistry
Publication Status: Published
Online Publication Date: 2020-03-31
Appears in Collections:Chemistry