This paper considers the total synthesis of a cellular differentiation regulator of , clostrienose, which is a unique fatty-acid glycosyl ester consisting of clostrienoic acid, (3,5,8,10)-3-hydroxy-tetradeca-5,8,10-trienoic acid and α-d-galactofuranosyl-(1 → 2)-α-l-rhamnose. The key features of our synthesis include stereoselective construction of a skipped-triene system in clostrienoic acid and its esterification with a disaccharide residue. The partially protected clostrienoic acid employed for the coupling also served for the preparation of l-rhamnosyl clostrienoate, thus leading to confirmation of the proposed structure unambiguously.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10536848 | PMC |
| http://dx.doi.org/10.1021/acsomega.3c05277 | DOI Listing |
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Total Synthesis of Clostrienose.
ACS Omega
September 2023
RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan.
This paper considers the total synthesis of a cellular differentiation regulator of , clostrienose, which is a unique fatty-acid glycosyl ester consisting of clostrienoic acid, (3,5,8,10)-3-hydroxy-tetradeca-5,8,10-trienoic acid and α-d-galactofuranosyl-(1 → 2)-α-l-rhamnose. The key features of our synthesis include stereoselective construction of a skipped-triene system in clostrienoic acid and its esterification with a disaccharide residue. The partially protected clostrienoic acid employed for the coupling also served for the preparation of l-rhamnosyl clostrienoate, thus leading to confirmation of the proposed structure unambiguously.
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