Helv. Chim. Acta 2019, 102, e1900131
[15] J. Kobayashi, K. Shimbo, S. Kubota, M. Tsuda, ‘Bioactive
References
macrolides and polyketides from marine dinoflagellates’,
Pure Appl. Chem. 2003, 75, 337–342.
[16] G. Valot, C. Regens, D. O’Malley, E. Godineau, H. Takikawa,
A. Fürstner, ‘Total Synthesis of Amphidinolide F’, Angew.
Chem. Int. Ed. 2013, 52, 9534–9538.
[17] T. D. Aicher, K. R. Buszek, F. G. Fang, C. J. Forsyth, S. H.
Jung, Y. Kishi, M. C. Matelich, P. M. Scola, D. M. Spero, S. K.
Yoon, ‘Total synthesis of halichondrin B and norhalichon-
drin B’, J. Am. Chem. Soc. 1992, 114, 3162–3164.
[18] G. Valot, D. Mailhol, C. Regens, D. O’Malley, E. Godineau, H.
Takikawa, P. Philipps, A. Fürstner, ‘Concise Total Syntheses
of Amphidinolides C and F’, Chem. Eur. J. 2015, 21, 2398–
2408.
[19] D. K. Mohapatra, P. Dasari, H. Rahaman, R. Pal, ‘Stereo-
selective synthesis of the densely functionalized C1–C9
fragment of amphidinolides C and F’, Tetrahedron Lett.
2009, 50, 6276–6279.
[1] K. Kong, D. Romo, C. Lee, ‘Enantioselective Total Synthesis
of the Marine Toxin (À )-Gymnodimine Employing
a
Barbier-Type Macrocyclization’, Angew. Chem. Int. Ed. 2009,
48, 7402–7405.
[2] K. Kong, Z. Moussa, C. Lee, D. Romo, ‘Total Synthesis of the
Spirocyclic Imine Marine Toxin (À )-Gymnodimine and an
Unnatural C4-Epimer’, J. Am. Chem. Soc. 2011, 133, 19844–
19856.
[3] M. Litaudon, J. B. Hart, J. W. Blunt, R. J. Lake, M. Munro,
‘Isohomohalichondrin B,
a new antitumour polyether
macrolide from the New Zealand deep-water sponge
Lissodendoryx sp.’, Tetrahedron Lett. 2010, 35, 9435–9438.
[4] M. Nakamura, T. Ohno, S. Kunimoto, H. Naganawa, T.
Takeuchi, ‘Kijimicin: An Inhibitor of Human Immunodefi-
ciency Virus in Acutely and Chronically Infected Cells’, J.
Antibiot. 1991, 44, 569–571.
[5] L. K. Steinrauf, M. Pinkerton, J. W. Chamberlin, ‘The struc-
ture of nigericin’, Biochem. Biophys. Res. Commun. 1968, 33,
29–31.
[6] M. Akakabe, K. Kumagai, M. Tsuda, Y. Konishi, A. Tominaga,
M. Tsuda, E. Fukushi, J. Kawabata, ‘Iriomoteolide-13a, a
cytotoxic 22-membered macrolide from a marine dino-
flagellate Amphidinium species’, Tetrahedron 2014, 70,
2962–2965.
[20] C. Song, H. Liu, M. Hong, Y. Liu, F. Jia, L. Sun, Z. Pan, J.
Chang, ‘Convergent Formal Synthesis of (�)-Roseophilin’, J.
Org. Chem. 2012, 77, 704 À 706.
[21] Y. Liu, Y. Guo, F. Ji, D. Gao, C. Song, J. Chang, ‘Divergent
Syntheses of Carbazole Alkaloids Clausenapin, Indizoline,
Claulansine M, and Clausenaline D’, J. Org. Chem. 2016, 81,
4310–4315.
[22] T. Kubota, M. Tsuda, J. Kobayashi, ‘Absolute Stereochemis-
try of Amphidinolide C’, Org. Lett. 2001, 3, 1363–1366.
[23] R. H. Bates; J. B. Shotwell, W. R. Roush, ‘Stereoselective
Syntheses of the C(1)–C(9) Fragment of Amphidinolide C’,
Org. Lett. 2008, 10, 4343–4346.
[7] V. Havlíček, M. Ryska, S. Pospíšil, ‘Negative-ion fast atom
bombardment tandem mass spectrometry of sodium salts
of monensins and related compounds’, J. Mass Spectrom.
1995, 30, 1089–1094.
[8] M. Heinrich, J. J. Murphy, M. K. Ilg, A. Letort, J. Flasz, P.
Philipps, A. Fürstner, ‘Total Synthesis of Putative Chagosen-
sine’, Angew. Chem. Int. Ed. 2018, 57, 13575–13581.
[9] T. Řezanka, L. Hanuš, V. Dembitsky, ‘Chagosensine, a New
Chlorinated Macrolide from the Red Sea Sponge Leucetta
chagosensis’, Eur. J. Org. Chem. 2003, 4073–4079.
[10] G. Nakamura, K. Kobayashi, T. Sakurai, K. Isono, ‘Cationo-
mycin, a New Polyether Ionophore Antibiotic Produced by
Actinomadura nov. sp.’, J. Antibiot. 1981, 34, 1513–1514.
[11] G. Nakamura, K. Isono, ‘A New Species Of Actinomadura
Producing a Polyether Antibiotic, Cationomycin’, J. Antibiot.
1983, 36, 1468–1472.
[24] M. P. Paudyal, N. P. Rath, C. D. Spilling, ‘A Formal Synthesis
of the C1–C9 Fragment of Amphidinolide C Employing the
Tamaru Reaction’, Org. Lett. 2010, 12, 2954–2957.
[25] J. S. Clark, G. Yang, A. P. Osnowski, ‘Synthesis of the C-1–C-
17 Fragment of Amphidinolides C, C2, C3, and F’, Org. Lett.
2013, 15, 1460–1463.
[26] J. S. Clark, G. Yang, A. P. Osnowski, ‘Synthesis of the C-18–
C-34 Fragment of Amphidinolides C, C2, and C3’, Org. Lett.
2013, 15, 1464–1467.
[27] S. Mahapatra, R. G. Carter, ‘Exploiting Hidden Symmetry in
Natural Products: Total Syntheses of Amphidinolides C and
F’, J. Am. Chem. Soc. 2013, 135, 10792–10803.
[28] J. Wang, J. Wang, C. Li, Y. Meng, J. Wu, C. Song, J. Chang,
‘Synthesis of 5-epi-Taiwaniaquinone G’, J. Org. Chem. 2014,
79, 6354–6359.
[12] J. Kobayashi, ‘Amphidinolides and Its Related Macrolides
from Marine Dinoflagellates’, J. Antibiot. 2008, 61, 271–
284.
[29] S. Mahapatra, R. G. Carter, ‘Enantioselective Total Synthesis
of Amphidinolide F’, Angew. Chem. Int. Ed. 2012, 51, 7948–
7951.
[13] J. Kobayashi, M. Ishibashi, ‘Bioactive Metabolites of Sym-
biotic Marine Microorganisms’, Chem. Rev. 1993, 93, 1753–
1769.
[14] J. Kobayashi, M. Tsuda, ‘Amphidinolides, Bioactive Macro-
lides from Symbiotic Marine Dinoflagellates’, Nat. Prod.
Rep. 2004, 21, 77–93.
Received May 14, 2019
Accepted June 6, 2019
(4 of 4) e1900131
© 2019 Wiley-VHCA AG, Zurich, Switzerland