A study towards the synthesis of (–)-atrop-abyssomicin C core Scientific paper

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Radomir N. Saičić
http://orcid.org/0000-0003-3653-8294
Milena Trmčić
https://orcid.org/0000-0002-6162-5755

Abstract

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 d-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) Delta7-unsaturated esters, which required the development of a new strategy for this type of transformation.

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How to Cite
[1]
R. N. Saičić and M. Trmčić, “A study towards the synthesis of (–)-atrop-abyssomicin C core: Scientific paper”, J. Serb. Chem. Soc., vol. 86, no. 12, pp. 1305–1315, Dec. 2021.
Section
Theme issue honoring Professor Emeritus Slobodan Milosavljevićs 80th birthday

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