Year: 2001
Type: article
Abstract: The total synthesis of madindolin A was achieved. Stereoselective construction of the quaternary carbon in the cyclopentenedione moiety was accomplished by alkylation of dienolate bearing a chiral auxiliary. The coupling of sterically hindered aldehyde 17 and acid-sensitive amine 30 was achieved by developing a new reductive amination method using Sn (OTf)2 and NaBH(OAc)3. After the reductive coupling, the cyclopentenedione skeleton of madindoline was constructed by intramolecular condensation of triketone 5.
Authors: Seijiro Hosokawa, Susumu Kobayashi
Institution: Tokyo University of Science
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
Funder: Kitasato University
OpenAlex ID: W2099226806