Synthesis of Functionalized Ring C of Escobarines

A synthetic strategy was developed for the preparation of α‐ethynyl‐α,β‐epoxy‐β‐formyl‐ and α‐ethynyl‐α,β‐epoxy‐β‐(hydroxymethyl)cyclohexanone from cyclohexenone as a model study in a proposed synthesis of escobarines. This highly functionalized ring is found in the anti‐TB cassane‐type diterpenes e...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-01, Vol.2016 (1), p.51-54
Main Authors: Lechuga-Eduardo, Harim, Romero-Ortega, Moises, Olivo, Horacio F.
Format: Article
Language:English
Subjects:
Epoxidation
Iodination
Sonagashira coupling
Synthetic methods
Umpolung
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Summary:A synthetic strategy was developed for the preparation of α‐ethynyl‐α,β‐epoxy‐β‐formyl‐ and α‐ethynyl‐α,β‐epoxy‐β‐(hydroxymethyl)cyclohexanone from cyclohexenone as a model study in a proposed synthesis of escobarines. This highly functionalized ring is found in the anti‐TB cassane‐type diterpenes escobarines A and B. Introduction of the β‐hydroxymethyl group was carried out by reversing the chemical reactivity of the enone using the anion of a sulfonyl group and electrophilic attack of paraformaldehyde. Further functionalization of the β‐(hydroxymethyl)cyclohexenone delivered the desired compounds. A hydroxymethyl group was introduced into C3 of cyclohexenone applying the umpolung concept. (Hydroxymethyl)cyclohexenone was properly functionalized to provide α‐acetylene‐α,β‐epoxy‐β‐formyl and α‐acetylene‐α,β‐epoxy‐β‐(hydroxymethyl)cyclohexanone as a model study for a proposed syntheses of escobarines A and B.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201501312