Total synthesis of madindoline A

Seijiro Hosokawa, Susumu Kobayashi

Research output: Contribution to journalArticle

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
Publication statusPublished - 2001 Nov
Externally publishedYes

Fingerprint

Bearings (structural)
Amination
Alkylation
Aldehydes
Amines
Condensation
Carbon
Acids
madindoline A

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Total synthesis of madindoline A. / Hosokawa, Seijiro; Kobayashi, Susumu.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 59, No. 11, 11.2001, p. 1103-1108.

Research output: Contribution to journalArticle

@article{bb9ef88394b146c2bf411bd58aba26d5,
title = "Total synthesis of madindoline A",
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.",
author = "Seijiro Hosokawa and Susumu Kobayashi",
year = "2001",
month = "11",
language = "English",
volume = "59",
pages = "1103--1108",
journal = "Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry",
issn = "0037-9980",
publisher = "Society of Synthetic Organic Chemistry",
number = "11",

}

TY - JOUR

T1 - Total synthesis of madindoline A

AU - Hosokawa, Seijiro

AU - Kobayashi, Susumu

PY - 2001/11

Y1 - 2001/11

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0035519734&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035519734&partnerID=8YFLogxK

M3 - Article

VL - 59

SP - 1103

EP - 1108

JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

SN - 0037-9980

IS - 11

ER -