Inter‐ and Intramolecular Hetero Diels‐Alder Reactions, 31. Synthesis of D‐Homoestrone Derivatives by Tandem Knoevenagel Hetero Diels‐Alder Reactions from Natural Estrone

Lutz F. Tietze, J. Wölfling, G. Schneider

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The tandem Knoevenagel hetero Diels‐Alder reaction of the secoestrone derivative 8 with dimethylbarbituric acid (9a). Meldrum's acid (9b), and the pyrazolones 13a–c stereoselectively affords the D‐homoestrone derivatives 11a, 12, and 14a–c, respectively, with the 16α,17aα configuration in excellent yield. In the reaction of 8 with 9a, b only one diastereomer can be detected, whereas in the reaction of 8 with 13a–c a small amount of the isomeric adducts 15a–c has also been found.

Original languageEnglish
Pages (from-to)591-594
Number of pages4
JournalChemische Berichte
Volume124
Issue number3
DOIs
Publication statusPublished - 1991

Fingerprint

Estrone
Pyrazolones
Derivatives
Acids
Meldrum's acid

Keywords

  • D‐Homoestrones
  • Hetero Diels‐Alder reaction
  • Knoevenagel reaction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

@article{1770ced4ce604fc58e3212c4c90c4224,
title = "Inter‐ and Intramolecular Hetero Diels‐Alder Reactions, 31. Synthesis of D‐Homoestrone Derivatives by Tandem Knoevenagel Hetero Diels‐Alder Reactions from Natural Estrone",
abstract = "The tandem Knoevenagel hetero Diels‐Alder reaction of the secoestrone derivative 8 with dimethylbarbituric acid (9a). Meldrum's acid (9b), and the pyrazolones 13a–c stereoselectively affords the D‐homoestrone derivatives 11a, 12, and 14a–c, respectively, with the 16α,17aα configuration in excellent yield. In the reaction of 8 with 9a, b only one diastereomer can be detected, whereas in the reaction of 8 with 13a–c a small amount of the isomeric adducts 15a–c has also been found.",
keywords = "D‐Homoestrones, Hetero Diels‐Alder reaction, Knoevenagel reaction",
author = "Tietze, {Lutz F.} and J. W{\"o}lfling and G. Schneider",
year = "1991",
doi = "10.1002/cber.19911240327",
language = "English",
volume = "124",
pages = "591--594",
journal = "Chemische Berichte",
issn = "0009-2940",
publisher = "John Wiley and Sons Ltd",
number = "3",

}

TY - JOUR

T1 - Inter‐ and Intramolecular Hetero Diels‐Alder Reactions, 31. Synthesis of D‐Homoestrone Derivatives by Tandem Knoevenagel Hetero Diels‐Alder Reactions from Natural Estrone

AU - Tietze, Lutz F.

AU - Wölfling, J.

AU - Schneider, G.

PY - 1991

Y1 - 1991

N2 - The tandem Knoevenagel hetero Diels‐Alder reaction of the secoestrone derivative 8 with dimethylbarbituric acid (9a). Meldrum's acid (9b), and the pyrazolones 13a–c stereoselectively affords the D‐homoestrone derivatives 11a, 12, and 14a–c, respectively, with the 16α,17aα configuration in excellent yield. In the reaction of 8 with 9a, b only one diastereomer can be detected, whereas in the reaction of 8 with 13a–c a small amount of the isomeric adducts 15a–c has also been found.

AB - The tandem Knoevenagel hetero Diels‐Alder reaction of the secoestrone derivative 8 with dimethylbarbituric acid (9a). Meldrum's acid (9b), and the pyrazolones 13a–c stereoselectively affords the D‐homoestrone derivatives 11a, 12, and 14a–c, respectively, with the 16α,17aα configuration in excellent yield. In the reaction of 8 with 9a, b only one diastereomer can be detected, whereas in the reaction of 8 with 13a–c a small amount of the isomeric adducts 15a–c has also been found.

KW - D‐Homoestrones

KW - Hetero Diels‐Alder reaction

KW - Knoevenagel reaction

UR - http://www.scopus.com/inward/record.url?scp=84985653048&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84985653048&partnerID=8YFLogxK

U2 - 10.1002/cber.19911240327

DO - 10.1002/cber.19911240327

M3 - Article

VL - 124

SP - 591

EP - 594

JO - Chemische Berichte

JF - Chemische Berichte

SN - 0009-2940

IS - 3

ER -