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. 2017 Apr 7;19(7):1698-1701.
doi: 10.1021/acs.orglett.7b00418. Epub 2017 Mar 28.

Enantioselective Synthesis of (-)-Acetylapoaranotin

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Free PMC article

Enantioselective Synthesis of (-)-Acetylapoaranotin

Haoxuan Wang et al. Org Lett. .
Free PMC article

Abstract

The first enantioselective total synthesis of the epipolythiodiketopiperazine (ETP) natural product (-)-acetylapoaranotin (3) is reported. The concise synthesis was enabled by an eight-step synthesis of a key cyclohexadienol-containing amino ester building block. The absolute stereochemistry of both amino ester building blocks used in the synthesis is set through catalytic asymmetric (1,3)-dipolar cycloaddition reactions. The formal syntheses of (-)-emethallicin E and (-)-haemotocin are also achieved through the preparation of a symmetric cyclohexadienol-containing diketopiperazine.

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Representative ETP natural products and retrosynthetic analysis.
Scheme 1
Scheme 1. Enantioselective Synthesis of 7
Scheme 2
Scheme 2. Completion of the Synthesis of (−)-Acetylapoaranotin (3)
Scheme 3
Scheme 3. Synthesis of DKP 26, an Intermediate in the Formal Syntheses of Emethallicin E (4) and Haematocin (27)

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