Total synthesis of madindoline A

Seijiro Hosokawa, Susumu Kobayashi

Research output: Contribution to journalReview article

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1103-1108
Number of pages6
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume59
Issue number11
DOIs
Publication statusPublished - 2001 Nov
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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