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Review
. 2003:60:207-85.
doi: 10.1016/s0099-9598(03)60004-0.

The manzamine alkaloids

Jin-Feng Hu  1 , Mark T Hamann, Russell Hill, Michelle Kelly
Affiliations
Review

The manzamine alkaloids

Jin-Feng Hu et al. Alkaloids Chem Biol. 2003.
No abstract available

PubMed Disclaimer

Figures

Figure 1.
Figure 1.
The structures of manzamine A (1) and its hydrochloride (1a).
Figure 2.
Figure 2.
β-Carboline-containing manzamines.
Figure 2.
Figure 2.
β-Carboline-containing manzamines.
Figure 2.
Figure 2.
β-Carboline-containing manzamines.
Figure 3.
Figure 3.
Manzamine-related marine alkaloids.
Figure 3.
Figure 3.
Manzamine-related marine alkaloids.
Figure 3.
Figure 3.
Manzamine-related marine alkaloids.
Figure 4.
Figure 4.
Recently isolated β-carboline manzamine alkaloids.
Fig. 5.
Fig. 5.
Neighbor-joining phylogenetic tree from analysis of ca. 500 bp of 16S rRNA gene sequence from clones obtained from Acanthostrongylophora sp. (01IND035) (58). The scale bar represents 0.1 substitutions per nucleotide position. Culturable isolates from the sponge are boxed. Sequences shown in bold are those whose nearest relatives, based on BLAST searches, are also from sponges.
Scheme 1.
Scheme 1.
Biogenetic path of manzamines A (1), B (2), and C (3) proposed by Baldwin et al. (5).
Scheme 2.
Scheme 2.
Biogenetic Pathway for Manzamine C (3) Proposed by Tsuda et al. (2).
Scheme 3.
Scheme 3.
Biogenesis of ingenamine (44), proposed by Kong et al. (31).
Scheme 4.
Scheme 4.
Biogenesis of nakadomarin A (56) from ircinal A (35) (3,57).
Scheme 5.
Scheme 5.
Biogenesis of the 12,34-oxaether bridge in alkaloid 58 (58).
Scheme 6.
Scheme 6.
Biogenetic pathway of manadomanzamine A (62) and B (63) (59).
Scheme 7.
Scheme 7.
Synthesis of Manzamine C (3) by Torisawa et al. (66,67).
Scheme 8.
Scheme 8.
Synthesis of the pentacyclic core of manzamine A (1) by Pandit et al. (74).
Scheme 9.
Scheme 9.
Synthesis of the tetracyclic core of manzamine A (1) by Nakagawa et al. (75).
Scheme 10.
Scheme 10.
The Total Synthesis of Ircinal A (35), Ircinol A (37), Manzamines A (1) and D (4) by Winkler et al. (76).
Scheme 11.
Scheme 11.
Semisynthesis of Manzamines A (1), D (4), H (8) and J (9) via Pictet–Spengler Cyclization (2,10).
Scheme 12.
Scheme 12.
Biomimetic Transformations among Manzamines A (1), X (12), and Y (13) (14).
Scheme 13.
Scheme 13.
Biogenetic Pathway of Xestomanzamines A (27) and B (28) (14)
Scheme 14.
Scheme 14.
Conversion of Ircinals A (35) and B (36) into their Alcohol Forms (35a and 36a) (2,25).
See this image and copyright information in PMC

References

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