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 language | English (US) |
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Pages (from-to) | 1831-1834 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 2 |
Issue number | 13 |
State | Published - Jun 29 2000 |
ASJC Scopus subject areas
- Molecular Medicine