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Review
. 2024 Apr 2;29(7):1590.
doi: 10.3390/molecules29071590.

Recent Advances in the Synthesis of the Marine-Derived Alkaloid Fascaplysin and Its Metabolites Homofascaplysins A-C

Ramana Reddy Mittapalli  1 , Harshita Kumari  1
Affiliations
Review

Recent Advances in the Synthesis of the Marine-Derived Alkaloid Fascaplysin and Its Metabolites Homofascaplysins A-C

Ramana Reddy Mittapalli et al. Molecules. .

Abstract

The fascaplysin and homofascaplysin class of marine natural products has a characteristic 12H-pyrido[1,2-a:3,4-b']diindole pentacyclic structure. Fascaplysin was isolated in 1988 from the marine sponge Fascaplysinopsis bergquist sp. The analogs of fascaplysin, such as homofascaplysins A, B, and C, were discovered late in the Fijian sponge F. reticulate, and also have potent antimicrobial activity and strong cytotoxicity against L-1210 mouse leukemia. In this review, the total synthesis of fascaplysin and its analogs, such as homofascaplysins A, B, and C, will be reviewed, which will offer useful information for medicinal chemistry researchers who are interested in the exploration of marine alkaloids.

Keywords: alkaloids; fascaplysin; homofascaplysins A, B, and C; marine natural products; sponge.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
Structures of fascaplysin and homofascaplysins A–C.
Scheme 1
Scheme 1
First total synthesis of fascaplysin by Gribble et al. [23].
Scheme 2
Scheme 2
Total synthesis of fascaplysin by Qukguiner et al. [24].
Scheme 3
Scheme 3
Total synthesis of fascaplysin by Molina et al. [25].
Scheme 4
Scheme 4
Total synthesis of fascaplysin from tryptamine.
Scheme 5
Scheme 5
Total synthesis of fascaplysin via a silver-catalyzed cascade reaction.
Scheme 6
Scheme 6
Total synthesis of fascaplysin using Fischer cyclization as a key step.
Scheme 7
Scheme 7
Total synthesis of fascaplysin from tryptamine.
Scheme 8
Scheme 8
Two-step synthesis of fascaplysin under microwave conditions.
Scheme 9
Scheme 9
Total synthesis of fascaplysin from indigo.
Scheme 10
Scheme 10
Formal synthesis of fascaplysin via pyrone remodeling.
Scheme 11
Scheme 11
Total synthesis of fascaplysin from tryptamine by UV irradiation.
Scheme 12
Scheme 12
First total synthesis of homofascaplysins B and C from indole.
Scheme 13
Scheme 13
Total synthesis of homofascaplysin C from 3-methylindole.
Scheme 14
Scheme 14
Total synthesis of homofascaplysin C from ditryptophan esters.
Scheme 15
Scheme 15
Total synthesis of homofascaplysin C via a silver-catalyzed cascade reaction.
Scheme 16
Scheme 16
Total synthesis of homofascaplysins B and C through photocyclization/dehydrogenation reactions.
Scheme 17
Scheme 17
Total synthesis of homofascaplysin C from α-diazoketones.
Scheme 18
Scheme 18
One-step transformation of the marine alkaloid fascaplysin into homofascaplysin B.
See this image and copyright information in PMC

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