Intramolecular Diels-Alder reactions of decatrienoates: Remote stereocontrol and conformational activation

Pilho Kim, Michael H. Nantz, Mark J. Kurth, Marilyn M. Olmstead

Research output: Contribution to journalArticle

36 Scopus citations

Abstract

(Formula presented) The intramolecular Diels-Alder (IMDA) reactions of C(8)-substituted decatrienoates have been studied. The stereospecific formation of 11 via an endo-boat-9 transition state attests to the powerful directing influence of a C(8) substituent in the IMDA of decatrienoate. In addition, the contrasting observations that stereospecific 9 → 11 occurs at room temperature while the nor-tert-butyl substrate (4a) requires 125 °C/5 h reaction conditions and produces a 60:40 mixture of diastereomers provide clear evidence that a bulky C(8) substituent is a powerful conformational activator of the IMDA.

Original languageEnglish (US)
Pages (from-to)1831-1834
Number of pages4
JournalOrganic Letters
Volume2
Issue number13
StatePublished - Jun 29 2000

ASJC Scopus subject areas

  • Molecular Medicine

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    Kim, P., Nantz, M. H., Kurth, M. J., & Olmstead, M. M. (2000). Intramolecular Diels-Alder reactions of decatrienoates: Remote stereocontrol and conformational activation. Organic Letters, 2(13), 1831-1834.