Nitro trienes 1, 2, and 3 are prepared from nona-5,7-dien-1-ols 6, 10, and 14, respectively, via a three-step sequence involving PCC oxidation, nitro aldol condensation, and dehydration. Intramolecular Diels-Alder reaction of nitro trienes 1 and 2 preferentially affords endo cycloadducts possessing the trans ring fusion (9:1 trans/cis) while cyclization of 3 gives exclusively the trans-fused perhydroindene skeleton (25c/25d, 9:1). In contrast, (Z)-nitroolefins 4 and 5, which are found to undergo cyclization at room temperature, produce a nearly 1:1 mixture of cis- and trans-fused cycloadducts.
|Original language||English (US)|
|Number of pages||7|
|Journal||Journal of Organic Chemistry|
|State||Published - 1985|
ASJC Scopus subject areas
- Organic Chemistry