Divergent Asymmetric Total Synthesis of Mulinane Diterpenoids

A concise, divergent, asymmetric total syntheses of mulinane diterpenoids has been achieved. Specifically, a new strategy was developed featuring a key intramolecular Friedel–Crafts reaction to construct the chiral fused 5‐6‐6 tricyclic motif, followed by sequential Birch reduction, conjugate methyl...

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Veröffentlicht in:Angewandte Chemie 2017-10, Vol.129 (41), p.12882-12885
Hauptverfasser: Liu, Yun‐Ting, Li, Lin‐Ping, Xie, Jian‐Hua, Zhou, Qi‐Lin
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Sprache:eng
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Zusammenfassung:A concise, divergent, asymmetric total syntheses of mulinane diterpenoids has been achieved. Specifically, a new strategy was developed featuring a key intramolecular Friedel–Crafts reaction to construct the chiral fused 5‐6‐6 tricyclic motif, followed by sequential Birch reduction, conjugate methylation, and homologation/ring‐expansion reactions to furnish the desired 5‐6‐7 tricyclic skeleton bearing five contiguous stereocenters. With this efficient strategy, seven mulinane diterpenoids and two analogues were synthesized via late‐stage functional modification or functionalization in 8.6–20 % overall yields and 11–15 steps. Asymmetrische Totalsynthesen von Mulinan‐Diterpenoiden liefern in direkter und divergenter Weise sieben Naturstoffe und zwei Analoga in 8.6–20 % Gesamtausbeute nach 11–15 Stufen.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201706994