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Enantiospecific Total Synthesis of (−)‐Hyacinthacine A1 and (+)‐Hyacinthacine A1 and Their Homologues Using Nitrogen Substituted Donor–Acceptor Cyclopropane.
- Source :
-
European Journal of Organic Chemistry . 11/2/2023, Vol. 26 Issue 41, p1-5. 5p. - Publication Year :
- 2023
-
Abstract
- A concise and efficient enantiospecific total synthesis of (−)‐hyacinthacine A1 and (+)‐hyacinthacine A1 was achieved from commercially available starting material L‐pyroglutamic acid and D‐glutamic acid, respectively. For the synthesis of this trihydroxylated pyrrolizidine ring, we employed the nitrogen‐substituted donor‐acceptor cyclopropane as a key intermediate. The synthetic approach relies on two crucial steps, highly stereo‐ and regioselective intramolecular cyclopropanation with Rh2(OAc)4 and regioselective ring opening of a nitrogen‐substituted donor‐acceptor cyclopropane. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CYCLOPROPANE
*CYCLOPROPANATION
*PYRROLIZIDINES
*CYCLOPROPANE derivatives
*NITROGEN
Subjects
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 26
- Issue :
- 41
- Database :
- Academic Search Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 173454971
- Full Text :
- https://doi.org/10.1002/ejoc.202300818