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. Author manuscript; available in PMC: 2019 Jan 30.
Published in final edited form as: Nat Catal. 2018 Jul 30;1(8):609–615. doi: 10.1038/s41929-018-0115-4

Figure 1. Comparison of the total synthesis and the biosynthesis6 of isolongifolene3, 4 and longifolene5.

Figure 1

In the total syntheses, long synthetic sequences were required for the stepwise construction of the skeleton of isolongifolene and longifolene. In contrast, by utilizing linear farnesyl pyrophosphate as the substrate, the natural enzyme directly accesses longifolene via cyclisation-rearrangement cascade reaction. Acid-catalysed rearrangement reaction of longifolene is known to produce isolongifolene. However, the biosynthesis of isolongifolene is unknown.