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Studies on the total synthesis of gibberellins. a new strategy for a-ring construction

Journal Article


Abstract


  • 3-(4', 6'-Dimethoxynaphthalen-1'-y1)propanoic acid (10) was transformed to 8-methoxy-5-(3'-oxo-buty1)-1, 2, 3, 4-tetrahydronaphthalene-2-carboxylic acid (8) and its 2-hydroxy derivative (9) by conventional synthetic reactions. Acid-catalysed cyclization of the derived diazomethyl ketones (23), (24) and (25) led to dienones (26), (27) and (28) which readily underwent base-catalysed 1, 4-conjugate addition to provide the hydroethanophenanthrenetriones (30), (31) and (32) respectively. © 1981, CSIRO. All rights reserved.

Publication Date


  • 1981

Citation


  • Ianlair, A., Mander, L. N., Mundill, P. H. C., & Pyne, S. G. (1981). Studies on the total synthesis of gibberellins. a new strategy for a-ring construction. Australian Journal of Chemistry, 34(9), 1887-1898. doi:10.1071/CH9811887

Scopus Eid


  • 2-s2.0-84918990339

Web Of Science Accession Number


Start Page


  • 1887

End Page


  • 1898

Volume


  • 34

Issue


  • 9

Abstract


  • 3-(4', 6'-Dimethoxynaphthalen-1'-y1)propanoic acid (10) was transformed to 8-methoxy-5-(3'-oxo-buty1)-1, 2, 3, 4-tetrahydronaphthalene-2-carboxylic acid (8) and its 2-hydroxy derivative (9) by conventional synthetic reactions. Acid-catalysed cyclization of the derived diazomethyl ketones (23), (24) and (25) led to dienones (26), (27) and (28) which readily underwent base-catalysed 1, 4-conjugate addition to provide the hydroethanophenanthrenetriones (30), (31) and (32) respectively. © 1981, CSIRO. All rights reserved.

Publication Date


  • 1981

Citation


  • Ianlair, A., Mander, L. N., Mundill, P. H. C., & Pyne, S. G. (1981). Studies on the total synthesis of gibberellins. a new strategy for a-ring construction. Australian Journal of Chemistry, 34(9), 1887-1898. doi:10.1071/CH9811887

Scopus Eid


  • 2-s2.0-84918990339

Web Of Science Accession Number


Start Page


  • 1887

End Page


  • 1898

Volume


  • 34

Issue


  • 9