Gold-catalyzed stereoselective cycloisomerization of allenoic acids for two types of common natural γ-butyrolactones

Jing Zhou, Chunling Fu and Shengming Ma ()
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Jing Zhou: Zhejiang University
Chunling Fu: Zhejiang University
Shengming Ma: Zhejiang University

Nature Communications, 2018, vol. 9, issue 1, 1-10

Abstract: Abstract γ-(E)-Vinylic and γ-alkylic γ-butyrolactones are two different types of lactones existing extensively in animals and plants and many of them show interesting biological activities. Nature makes alkylic γ-butyrolactones by many different enzymatic lactonization processes. Scientists have been mimicking the natural strategy by developing new catalysts. However, direct and efficient access to γ-(E)-vinylic γ-butyrolactones is still extremely limited. Here, we wish to present our modular allene approach, which provides an efficient asymmetric approach to (E)-vinylic γ-butyrolactones from allenoic acids by identifying a new gold complex as the catalyst. Based on this cycloisomerization strategy, the first syntheses of racemic xestospongiene and xestospongienes E, F, G, and H have been realized and the absolute configurations of the chiral centers in xestospongienes E and F have been revised. In addition, by applying a C–O bond cleavage-free hydrogenation, the syntheses of naturally occurring γ-alkylic γ-lactones, (R)-4-tetradecalactone, (S)-4-tetradecalactone, (R)-γ-palmitolactone, and (R)-4-decalactone, have also been achieved.

Date: 2018
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DOI: 10.1038/s41467-018-03894-6

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