An efficient and mild synthetic strategy for the total synthesis of selaginpulvilin D has been reported. A highly chemoselective enyne-alkyne dehydro Diels-Alder reaction has been employed for the construction of the tricyclic fluorene framework present in the natural product selaginpulvilin D. An improved overall yield (10.5%) has been achieved for selaginpulvilin D, starting from commercially available m-anisaldehyde in 9 linear, operationally simple synthetic transformations.
We report here a systematic study of the aromatic tetradehydro‐Diels–Alder (Ar‐TDDA) reaction to elucidate the factors that have significant effects on the distribution of linear and angular naphthalene products. Two factors were studied, that is, the nature of the linker and the steric bulk of the substituent of the enyne part. The structure of the linker has a tremendous effect on the product distribution. The effect of the steric bulk of the substituent is dependent on the linker structure, in other words, different preferences are observed for different linkers.
An efficient formal total synthesis of two compounds from the selaginpulvilin family of natural products, selaginpulvilin A and C, has been successfully achieved. The tetradehydro Diels-Alder (TDDA) reaction between an enyne and alkyne has been utilized for the creation of the necessary fluorene skeleton. Attempts at the conversion of selaginpulvilin A to selaginpulvilin B, F and H were unsuccessful.
Rapid synthesis of the [5‐5‐6‐6] tetracyclic system in the spirobionaphthalene natural product spiropreussione B was achieved. An intramolecular, thermal dehydrogenative Diels–Alder reaction was employed as the key step. Furthermore, this approach was extended to generate a library of structurally novel linear tetracyclic systems of spiropreussione B in a highly efficient manner. This report constitutes the first synthetic approach to the spiropreussione B natural product.
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