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- Title
Enantiospecific Total Synthesis of (−)‐Hyacinthacine A<sub>1</sub> and (+)‐Hyacinthacine A<sub>1</sub> and Their Homologues Using Nitrogen Substituted Donor–Acceptor Cyclopropane.
- Authors
Gharpure, Santosh J.; Patel, Raj K.
- 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.
- Subjects
CYCLOPROPANE; CYCLOPROPANATION; PYRROLIZIDINES; CYCLOPROPANE derivatives; NITROGEN
- Publication
European Journal of Organic Chemistry, 2023, Vol 26, Issue 41, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202300818