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. 2020 Dec 22;6(1):881-888.
doi: 10.1021/acsomega.0c05484. eCollection 2021 Jan 12.

Total Synthesis of Marine Alkaloids Motuporamines A and B via Ring Expansion of Cyclic β-Keto Esters

Zi-Jie Song  1 , Shu-Yu Meng  1 , Quan-Rui Wang  1
Affiliations

Total Synthesis of Marine Alkaloids Motuporamines A and B via Ring Expansion of Cyclic β-Keto Esters

Zi-Jie Song et al. ACS Omega. .

Abstract

An expedient total synthesis of the title marine sponge alkaloids has been developed. The salient features of the synthesis are as follows: (i) preparation of the required 13- and 14-membered cyclic lactams with n + 4 ring-expansion strategy of cyclic β-keto esters and (ii) functional group manipulation of the resulted keto ester lactams. This approach used easily accessible and inexpensive materials/reagents, thus providing a promising alternative to the existing preparations.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Structures of motuporamines A (1) and B (2).
Scheme 1
Scheme 1. Synthetic Route to 13-Membered Keto-Lactam 10
Scheme 2
Scheme 2. Synthesis of TFA Salt of Motuporamine A (1·TFA)
Scheme 3
Scheme 3. Synthetic Route to 14-Membered Keto-Lactam 22
Scheme 4
Scheme 4. Synthesis of TFA Salt of Motuporamine B (2·TFA)
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