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. 2007 Jan 7;64(2):261-298.
doi: 10.1016/j.tet.2007.10.039.

(+)-Discodermolide: Total Synthesis, Construction of Novel Analogues, and Biological Evaluation

Amos B Smith  1 , B Scott Freeze
Affiliations

(+)-Discodermolide: Total Synthesis, Construction of Novel Analogues, and Biological Evaluation

Amos B Smith et al. Tetrahedron. .
No abstract available

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Figures

Figure 1
Figure 1
Natural and non-natural microtubule-stabilizing agents.
Figure 2
Figure 2
Retrosynthetic analyses of (+)-discodermolide.
Figure 3
Figure 3
(+)-Discodermolide, (−)-discodermolide, and other Schreiber analogues.
Figure 4
Figure 4
Schreiber analogues of (+)-discodermolide.
Figure 5
Figure 5
Harbor Branch semi-synthetic analogues.
Figure 6
Figure 6
Harbor Branch – semi-synthetic analogues.
Figure 7
Figure 7
Harbor Branch – naturally occurring discodermolide congeners.
Figure 8
Figure 8
Paterson analogues of (+)-discodermolide.
Figure 9
Figure 9
Novartis analogues of (+)-discodermolide.
Figure 10
Figure 10
Novartis analogues of (+)-discodermolide.
Figure 11
Figure 11
Novartis/Harbor Branch synthetic analogues.
Figure 12
Figure 12
Curran/Day simplified analogues.
Figure 13
Figure 13
Smith and Smith/Kosan lactone-replacement analogues of (+)-discodermolide.
Figure 14
Figure 14
Smith aryl lactone-replacement analogues.
Figure 15
Figure 15
Smith coumarin-derived lactone replacement analogues
Figure 16
Figure 16
Smith 14-normethyl lactone-replacement analogues.
Figure 17
Figure 17
Smith diene-replacement analogues of (+)-14-normethyldiscodermolide.
Figure 18
Figure 18
Smith carbamate-substitution analogues of (+)-discodermolide.
Figure 19
Figure 19
Compounds evaluated as in vivo tumor suppression agents.
Scheme 1
Scheme 1
The Schreiber synthesis of fragments 5, 7, and 10.
Scheme 2
Scheme 2
The Schreiber total synthesis of discodermolide.
Scheme 3
Scheme 3
The Smith first-generation synthesis of fragments 16, 18, and 22.
Scheme 4
Scheme 4
The Smith first-generation total synthesis of discodermolide.
Scheme 5
Scheme 5
The Myles synthesis of fragments 30, 32, and 34.
Scheme 6
Scheme 6
The Myles total synthesis of discodermolide.
Scheme 7
Scheme 7
The Marshall synthesis of fragments (+)-44, (+)-48, and (−)-51.
Scheme 8
Scheme 8
The Marshall total synthesis of (+)-discodermolide.
Scheme 9
Scheme 9
The Evans synthesis of fragments (−)-58, (+)-62, and (+)-65.
Scheme 10
Scheme 10
The Evans total synthesis of (+)-discodermolide.
Scheme 11
Scheme 11
Smith gram-scale discodermolide retrosynthesis.
Scheme 12
Scheme 12
The Smith gram-scale synthesis of (−)-14 and (−)-72.
Scheme 13
Scheme 13
The Smith gram-scale total synthesis of (+)-discodermolide.
Scheme 14
Scheme 14
Third-generation improvements to the Smith gram-scale synthesis
Scheme 15
Scheme 15
Smith fourth-generation synthesis of (+)-discodermolide.
Scheme 16
Scheme 16
The Paterson first-generation synthesis of (+)-95, (+)-100, and (−)-103.
Scheme 17
Scheme 17
The Paterson first-generation total synthesis of (+)-discodermolide.
Scheme 18
Scheme 18
The Paterson second-generation synthesis of (+)-95, (+)-112, and (−)-114.
Scheme 19
Scheme 19
The Paterson second-generation total synthesis of (+)-discodermolide.
Scheme 20
Scheme 20
The Paterson third-generation synthesis of (+)-discodermolide.
Scheme 21
Scheme 21
The Novartis sixty-gram total synthesis of (+)-discodermolide.
Scheme 22
Scheme 22
The Panek synthesis of (+)-125, (−)-127, and (−)-129.
Scheme 23
Scheme 23
The Panek total synthesis of (+)-discodermolide.
See this image and copyright information in PMC

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