Total Synthesis of (−)-(2R)-Dihydromyricoidine

Total Synthesis of (−)-(2R)-Dihydromyricoidine

An asymmetric synthesis of the spermidine alkaloid (−)‐(2R)‐dihydromyricoidine (5) was performed by employing two ring‐enlargement reactions. The chiral center was introduced by a diastereoselective Michael addition of perhydropyridazine (7) to the α,β‐unsaturated ester 6. The (Z)‐CC bond was obtai...

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Veröffentlicht in:Helvetica chimica acta 1996-10, Vol.79 (7), p.1995-2003
Hauptverfasser: Häusermann, Ursula A., Linden, Anthony, Song, Jiangao, Hesse, Manfred
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container_end_page 2003
container_issue 7
container_start_page 1995
container_title Helvetica chimica acta
container_volume 79
creator Häusermann, Ursula A.
Linden, Anthony
Song, Jiangao
Hesse, Manfred
description An asymmetric synthesis of the spermidine alkaloid (−)‐(2R)‐dihydromyricoidine (5) was performed by employing two ring‐enlargement reactions. The chiral center was introduced by a diastereoselective Michael addition of perhydropyridazine (7) to the α,β‐unsaturated ester 6. The (Z)‐CC bond was obtained by a selective Wittig reaction. The synthetic compound 5 was found to have a negative value for the specific rotation. This is in contrast to that of the natural product reported in the literature. Therefore, as an outcome of this synthesis, the absolute configuration of the natural alkaloid should be inverted to be as shown in structure V.
doi_str_mv 10.1002/hlca.19960790721
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title Total Synthesis of (−)-(2R)-Dihydromyricoidine
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