Download PDF
Synlett 1995; 1995(1): 105-107
DOI: 10.1055/s-1995-4843
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Intramolecular Diels-Alder Reaction with Furan-Diene: Syntheses of Gibberellins (+)-GA1 and (+)-GA3

Frank Nuyttens, Jan Hoflack, Giovanni Appendino, Pierre J. De Clercq*
  • *University of Gent, Department of Organic Chemistry, Laboratory for Organic Synthesis, Krijgslaan, 281 (S.4), B-9000 GENT (Belgium)
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Total syntheses of GA1 and GA3 are described featuring the use of an intramolecular Diels-Alder reaction involving furan-diene for the construction of the tetracyclic kaurenoid skeleton, with the appropriate stereochemistry in the adduct for the selective transformation into gibberellins possessing a β-oriented 3-OH group. The synthesis further proceeds via contraction of the central B-ring to the required 5-membered ring size and requires the use of a relay intermediate for eventual completion.

IMDAF - furan-diene - ring contraction

      >