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Synthesis of Functionalized Ring C of Escobarines
Author(s) -
LechugaEduardo Harim,
RomeroOrtega Moises,
Olivo Horacio F.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501312
Subject(s) - chemistry , hydroxymethyl , cyclohexenone , cyclohexanone , enone , paraformaldehyde , ring (chemistry) , electrophile , surface modification , organic chemistry , stereochemistry , catalysis
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.