Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer | Zendy

Peňaška Tibor | Zendy; Koukal Petr | Zendy; Kotora Martin | Zendy

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Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer

Author(s) -

Peňaška Tibor,

Koukal Petr,

Kotora Martin

Publication year - 2018

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.201701416

Subject(s) - enantioselective synthesis , chemistry , epimer , stereochemistry , fragment (logic) , mandelic acid , organic chemistry , catalysis , computer science , programming language

The key aetheramide A intermediate with the natural ( R , R , R ) configuration along with the one having the unnatural ( R , S , R ) configuration was synthesized. The synthesis of both stereoisomers was accomplished by Suzuki coupling of two advanced chiral building blocks: ( R , R )‐ and ( R , S )‐vinylboronates and an ( R )‐iodoalkene. The former was prepared from ( R )‐mandelic acid, and the latter was prepared by enantioselective allylation of 3‐iodoacrylaldehyde.

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