Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.
Journal
Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056
Informations de publication
Date de publication:
20 02 2019
20 02 2019
Historique:
pubmed:
31
1
2019
medline:
8
7
2020
entrez:
31
1
2019
Statut:
ppublish
Résumé
The Illicium sesquiterpenes are a family of natural products containing over 100 highly oxidized and structurally complex members, many of which display interesting biological activities. This comprehensive account chronicles the evolution of a semisynthetic strategy toward these molecules from (+)-cedrol, seeking to emulate key aspects of their presumed biosynthesis. An initial route generated lower oxidation state analogs but failed in delivering a crucial hydroxy group in the final step. Insight gathered during these studies, however, ultimately led to a synthesis of the pseudoanisatinoids along with the allo-cedrane natural product 11- O-debenzoyltashironin. A second-generation strategy was then developed to access the more highly oxidized majucinoid compounds including jiadifenolide and majucin itself. Overall, one dozen natural products can be accessed from an abundant and inexpensive terpene feedstock. A multitude of general observations regarding site-selective C(sp
Identifiants
pubmed: 30698435
doi: 10.1021/jacs.8b12247
pmc: PMC6563921
mid: NIHMS1010808
doi:
Substances chimiques
Polycyclic Sesquiterpenes
0
Sesquiterpenes
0
cedrol
63ZM9703BO
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
3083-3099Subventions
Organisme : NIGMS NIH HHS
ID : P41 GM068933
Pays : United States
Organisme : NIGMS NIH HHS
ID : R01 GM116952
Pays : United States
Organisme : NCRR NIH HHS
ID : S10 RR027172
Pays : United States
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