Open AccessA study towards the synthesis of (-)-atrop-abyssomicin C core
Author(s) -
Radomir N. Saičić,
Milena Trmčić
Publication year - 2021
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc211001099s
Subject(s) - chemistry , combinatorial chemistry , protecting group , hydrolysis , lactone , radical cyclization , organic chemistry , alkyl
An attempt to synthesize the cyclohexane core of antibiotic abyssomicin C is described. The initial, protecting group-free approach (relying on internal protection) failed and had to be modified, in order to allow for efficient deprotection of the acid-sensitive cyclization precursor in the penultimate synthetic step. Thus, a pyranoside structural unit was used as a latent lactone/ester functionality, which was deprotected via thioacetalization/hydrolysis/oxidation sequence, to give the ?-valerolactone-type cyclization precursor. Unfortunately, the key cyclization reaction was not feasible, even after structural modification of the cyclization precursor. Reluctance towards cyclization turned out to be a general property of (at least some) ?7-unsaturated esters, which required the development of a new strategy for this type of transformation.