Retrosynthetic Analysis and Synthesis of Natural Products 1

Name: Retrosynthetic Analysis and Synthesis of Natural Products 1 | Synthetic Methods and Applications
Brand: Jossey-Bass
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Synthetic Methods and Applications

Olivier Piva(Autor*in)

Jossey-Bass (Verlag)

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Erschienen am 19. September 2019

320 Seiten

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Inhalt

Cover
Half-Title Page
Title Page
Copyright Page
Contents
Preface
1. Total Synthesis: Some Elements to Contemplate
1.1. Total synthesis - why and for what purpose?
1.2. The different approaches
1.3. Efficiency, selectivity
1.4. The essential reactions
1.5. Towards a sustainable total synthesis
1.6. What about tomorrow?
1.7. References
2. Squamostolide
2.1. Structure, isolation and properties
2.2. Bond disconnections
2.3. Approach according to M.J. Wu
2.3.1. Bond disconnections
2.3.2. Synthesis
2.3.3. Key reaction: Claisen-Ireland rearrangement
2.3.4. Key reaction: functionalization of true alkynes
2.3.5. Supporting synthetic transformations
2.4. Approach according to K.J. Quinn
2.4.1. Bond disconnections
2.4.2. Synthesis
2.4.3. Key reaction: alkene metathesis and tandem processes
2.4.4. Supporting synthetic transformations
2.5. References
3. Rubrenolide
3.1. Structure, isolation and properties
3.2. Disconnections
3.3. Approach according to H. Fujioka [FUJ 05, FUJ 08]
3.3.1. Disconnection
3.3.2. Synthesis, developed by the Fujioka group
3.3.3. Key reaction: iodoetherification
3.3.4. Key reaction: oxidation of aldehydes to carboxylic acids
3.3.5. Supporting synthetic transformations
3.4. Approach according to B. Zwanenburg
3.4.1. Retrosynthesis
3.4.2. Synthesis, Zwanenburg's approach
3.4.3. Key reaction: Wolff rearrangement
3.4.4. Key reaction: dehydration of alcohols according to Grieco
3.4.5. Supporting synthetic transformations
3.5. Approach according to N. Kommu [MAD 14]
3.5.1. Disconnections
3.5.2. Synthesis
3.5.3. Key reaction: diastereoselective alkylation of oxazolidinones
3.5.4. Key reaction: enantioselective reduction of ketones - CBS method
3.5.5. Key reaction: alkyne formation according to Ohira-Bestmann
3.5.6. Supporting synthetic transformations
3.6. References
4. Bipinnatin J
4.1. Structure, isolation and properties
4.2. Disconnections
4.3. Approach according to D. Trauner (racemic synthesis) [ROE 06a]
4.3.1. Synthesis
4.3.2. Key reaction: ene reaction between alkynes and alkenes
4.3.3. Key reaction: Stille coupling
4.3.4. Key reaction: Nozaki-Hiyama-Kishi reaction
4.3.5. Supporting synthetic transformations
4.4. Approach according to V.H. Rawal [HUA 06]
4.4.1. Synthesis
4.4.2. Key reaction: Negishi coupling
4.4.3. Supporting synthetic transformations
4.5. Enantioselective approach according to G. Pattenden [TAN 06]
4.5.1. Synthesis
4.5.2. Supporting synthetic transformations
4.6. Approach according to D. Trauner - enantioselective version
4.6.1. Synthesis [ROE 06b]
4.6.2. Supporting synthetic transformations
4.7. Comparison of the four syntheses
4.8. References
5. Tubingensin B
5.1. Structure, isolation and properties
5.2. Bond disconnections
5.3. Approach according to N.K. Garg
5.3.1. Bond disconnections
5.3.2. Synthesis
5.3.3. Key reaction: Sonogashira reaction
5.3.4. Key reaction: Suzuki coupling
5.3.5. Key reaction: cycloaddition [2+2] of arynes [HUT 11, GRE 86, TDA 12]
5.3.6. Key reaction: radical cyclization and Baldwin's rules
5.3.7. Key reaction: enantioselective hydrogenation of ketones
5.3.8. Supporting synthetic transformations
5.4. References
6. Polygonatine A
6.1. Structure, isolation and properties
6.2. Disconnections
6.3. Synthesis according to S.M. Allin
6.3.1. Disconnection
6.3.2. Synthesis
6.3.3. Key reaction: radical cyclization of selenoesters
6.3.4. Supporting synthetic transformations
6.4. Synthesis by J.P. Michael
6.4.1. Disconnections
6.4.2. Synthesis
6.4.3. Key reaction: Vilsmeier-Haack-Arnold reaction
6.4.4. Supporting synthetic transformations
6.5. References
7. (+)-Intricatetraol
7.1. Structure, isolation and properties
7.2. Disconnections
7.3. Approach according to Morimoto
7.3.1. Synthesis
7.3.2. Key reaction: epoxidation according to Katsuki-Sharpless
7.3.3. Key reaction: asymmetric epoxidation according to Shi
7.3.4. Supporting synthetic transformations
7.4. References
8. Enigmazole A
8.1. Structure, isolation and properties
8.2. Disconnections
8.3. Approach according to T. Molinski
8.3.1. Disconnections
8.3.2. Synthesis
8.3.3. Key reaction: 1,2-enantioselective addition of dialkylzinc to aldehydes
8.3.4. Key reaction: reduction of ß-aldols to 1,3-diols
8.3.5. Supporting synthetic transformations
8.4. Approach according to A. Fürstner
8.4.1. Disconnections
8.4.2. Synthesis
8.4.3. Key reaction: diastereoselective alkylation according to Myers
8.4.4. Key reaction: Yne-yne ring-closing metathesis (RCAM)
8.4.5. Key reaction: sigmatropic rearrangement [3,3] of propargyl esters
8.4.6. Supporting synthetic transformations
8.5. Approach according to A.B. Smith III
8.5.1. Disconnections
8.5.2. Synthesis
8.5.3. Key reaction: dithiane, umpolung and relayed reactions
8.5.4. Key reaction: Petasis-Ferrier rearrangement
8.5.5. Supporting synthetic transformations
8.6. Approach according to H. Fuwa
8.6.1. Disconnections
8.6.2. Synthesis
8.6.3. Key reaction: Tishchenko-Evans reaction
8.6.4. Key reaction: Meyer-Schuster and Rupe rearrangement
8.6.5. Supporting synthetic transformations
8.7. Comparative assessment of the different syntheses
8.8. References
9. Biyouyanagin A
9.1. Structure, isolation and properties
9.2. Synthesis according to K.C. Nicolaou
9.2.1. Disconnections [NIC 07, NIC 08]
9.2.2. Synthesis
9.2.3. Key reaction: 1,4-addition and organocatalysis
9.2.4. Shapiro reaction
9.2.5. Supporting synthetic transformations
9.3. References
10. Elatol
10.1. Structure, isolation and properties
10.2. Disconnections
10.3. Approach according to B. Stoltz
10.3.1. Disconnections
10.3.2. Synthesis
10.3.3. Key reaction: Tsuji-Trost reaction
10.3.4. Key reaction: ring-closing metathesis of hindered olefins
10.3.5. Key reaction: reduction of enones according to Luche
10.3.6. Supporting synthetic diagrams
10.4. References
11. Thiomarinol H
11.1. Structure, isolation and properties
11.2. Disconnections
11.3. Approach according to D.G. Hall
11.3.1. Disconnections
11.3.2. Synthesis
11.3.3. Key reaction: hetero-Diels-Alder enantioselective reaction
11.3.4. Supporting synthetic transformations
11.4. Approach according to S. Raghavan
11.4.1. Disconnections
11.4.2. Synthesis
11.4.3. Key reaction: Kirmse-Doyle rearrangement
11.4.4. Key reaction: Julia-Lythgoe and Julia-Kocienski reaction
11.4.5. Supporting synthetic transformations
11.5. References
12. Oblongolides A and C
12.1. Structures, isolation and properties
12.2. Disconnections
12.3. Synthesis of oblongolide A according to Shing
12.3.1. Disconnections
12.3.2. Synthesis
12.3.3. Key reaction: intramolecular Diels-Alder reaction
12.3.4. Supporting synthetic transformations
12.4. Shishido's approach to oblongolide C
12.4.1. Disconnections
12.4.2. Synthesis
12.4.3. Key reaction: intramolecular [3+2] cycloadditions
12.4.4. Supporting synthetic transformations
12.5. References
List of Abbreviations
Index
EULA

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