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. 2017 May 29;23(30):7180-7184.
doi: 10.1002/chem.201700499. Epub 2017 May 3.

Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation

Megan L Lanier  1   2 , Hyeri Park  1 , Paramita Mukherjee  1 , Jacob C Timmerman  1 , Anthony A Ribeiro  3 , Ross A Widenhoefer  1 , Jiyong Hong  1
Affiliations

Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation

Megan L Lanier et al. Chemistry. .

Abstract

8-Membered cyclic ethers are found in a wide range of natural products; however, they are challenging synthetic targets due to enthalpic and entropic barriers. The gold(I)-catalyzed intramolecular dehydrative alkoxylation of ω-hydroxy allylic alcohols was explored to stereoselectively construct α,α'-cis-oxocenes and further applied in a formal synthesis of (+)-laurencin. The gold(I)-catalyzed intramolecular dehydrative alkoxylation may constitute an alternative method for the synthesis of molecular building blocks and natural products that contain highly functionalized 8-membered cyclic ethers.

Keywords: (+)-laurencin; dehydrative alkoxylation; gold catalysis; natural products; ω-hydroxy allylic alcohols.

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Figures

Figure 1
Figure 1
Examples of naturally occurring 8-membered cyclic ethers.
Figure 2
Figure 2
The gold(I)-catalyzed intramolecular dehydrative alkoxylation approach to a stereoselective synthesis of (+)-laurencin (1).
Figure 3
Figure 3
Retrosynthetic plan for (+)-laurencin (1).
Scheme 1
Scheme 1
Preparation of epoxide and alkyne.
Scheme 2
Scheme 2
Formal synthesis of (+)-laurencin (1) via the gold(I)-catalyzed intramolecular dehydrative alkoxylation of ω-hydroxy allylic alcohol.
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