Stereoselective Synthesis of the C1-C16 Fragment of the Purported Structure of Formosalide B.
Journal
ACS omega
ISSN: 2470-1343
Titre abrégé: ACS Omega
Pays: United States
ID NLM: 101691658
Informations de publication
Date de publication:
05 May 2020
05 May 2020
Historique:
received:
01
04
2020
accepted:
10
04
2020
entrez:
12
5
2020
pubmed:
12
5
2020
medline:
12
5
2020
Statut:
epublish
Résumé
The first stereoselective synthesis of the C1-C16 fragment possessing stereo-enriched fully substituted tetrahydropyran (THP) along with tetrahydrofuran (THF) rings of the proposed structure of formosalide B is described in 12 longest linear steps with 22% overall yield, starting from two cheap and commercially available 1,5-pentanediol and l-glutamic acid, following a convergent approach. The key steps involve in this synthesis are Horner-Wadsworth-Emmons reaction, Sharpless asymmetric dihydroxylation, and acid-mediated ketalization to assemble the substituted THP ring, one-pot Sharpless dihydroxylation-S
Identifiants
pubmed: 32391510
doi: 10.1021/acsomega.0c01474
pmc: PMC7203982
doi:
Types de publication
Journal Article
Langues
eng
Pagination
10217-10224Informations de copyright
Copyright © 2020 American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
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