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1 article(s) from Donaldson, William A

Syntheses of spliceostatins and thailanstatins: a review

William A. Donaldson

Beilstein J. Org. Chem. 2020, 16, 1991–2006, doi:10.3762/bjoc.16.166

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Graphical Abstract

Figure 1: Structures of spliceostatins/thailanstatins.

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Scheme 1: Synthetic routes to protected (2Z,4S)-4-hydroxy-2-butenoic acid fragments.

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Scheme 2: Kitahara synthesis of the (all-cis)-2,3,5,6-tetrasubstituted tetrahydropyran.

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Scheme 3: Koide synthesis of (all-cis)-2,3,5,6-tetrasubstituted tetrahydropyran.

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Scheme 4: Nicolaou synthesis of the (all-cis)-2,3,5,6-tetrasubstituted tetrahydropyran.

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Scheme 5: Jacobsen synthesis of the (all-cis)-2,3,5,6-tetrasubstituted tetrahydropyran.

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Scheme 6: Unproductive attempt to generate the (all-cis)-tetrahydropyranone 50.

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Scheme 7: Ghosh synthesis of the C-7–C-14 (all-cis)-tetrahydropyran segment.

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Scheme 8: Ghosh’s alternative route to the (all-cis)-tetrahydropyranone 50.

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Scheme 9: Alternative synthesis of the dihydro-3-pyrone 58.

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Scheme 10: Kitahara’s 1st-generation synthesis of the C-1–C-6 fragment of FR901464 (1).

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Scheme 11: Kitahara 1st-generation synthesis of the C-1–C-6 fragment of FR901464 (1).

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Scheme 12: Nimura/Arisawa synthesis of the C-1-phenyl segment.

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Scheme 13: Ghosh synthesis of the C-1–C-6 fragment of FR901464 (1) from (R)-glyceraldehyde acetonide.

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Scheme 14: Jacobsen synthesis of the C-1–C-7 segment of FR901464 (1).

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Scheme 15: Koide synthesis of the C-1–C-7 segment of FR901464 (1).

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Scheme 16: Ghosh synthesis of the C-1–C-5 segment 102 of thailanstatin A (7).

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Scheme 17: Nicolaou synthesis of the C-1–C-9 segments of spliceostatin D (9) and thailanstatins A (7) and B (5...

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Scheme 18: Ghosh synthesis of the C-1–C-6 segment 115 of spliceostatin E (10).

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Scheme 19: Fragment coupling via Wittig and modified Julia olefinations by Kitahara.

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Scheme 20: Fragment coupling via cross-metathesis by Koide.

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Scheme 21: The Ghosh synthesis of spliceostatin A (4), FR901464 (1), spliceostatin E (10), and thailanstatin m...

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Scheme 22: Arisawa synthesis of a C-1-phenyl analog of FR901464 (1).

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Scheme 23: Jacobsen fragment coupling by a Pd-catalyzed Negishi coupling.

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Scheme 24: Nicolaou syntheses of thailanstatin A and B (7 and 5) and spliceostatin D (9) via a Pd-catalyzed Su...

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Scheme 25: The Ghosh synthesis of spliceostatin G (11) via Suzuki–Miyaura coupling.

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Review

Published 13 Aug 2020

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