List of Schemes
1.1 Steps 1–3 of the hederagonic acid (1) semisynthesis reported
by Wen et al. . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
1.2 Steps 4–6 of the hederagonic acid (1) semisynthesis reported
by Wen et al. . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
1.3 Steps 7–9 of the hederagonic acid (1) semisynthesis reported
by Wen et al. . . . . . . . . . . . . . . . . . . . . . . . . . . . 6
1.4 Stoichiometric C–H bond oxidation. . . . . . . . . . . . . . . 7
1.5 Selected applications of Baldwin’s cyclopalladation reaction. . 8
1.6 Catalytic C–H oxidation reported by the the Sanford Group.
9
1.7 Catalytic C–H oxidation of 2,2-dimethylpentanone oximes . . 10
1.8 Catalytic cycle of the C–H oxidation, proposed by the the
Sanford Group. . . . . . . . . . . . . . . . . . . . . . . . . . . 10
2.1 Concise synthesis of hederagonic acid (1) via catalytic C–H
oxidation. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
2.2 Synthesis of chlorolactone alcohol 26a. . . . . . . . . . . . . . 14
2.3 Synthesis of chlorolactone ketone 27a. . . . . . . . . . . . . . 15
2.4 Synthesis of chlorolactone oxime 6a. . . . . . . . . . . . . . . 15
2.5 C–H Acetoxylation of chlorolactone oxime 6a as performed
by Berger. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 16
2.6 One-pot deacetylation-deoximation of chlorolactone 7a. . . . 17
2.7 Retro-halolactonisation of bromolactone alcohol 26b. . . . . . 17
2.8 The formation of γ-butyrolactone from THF and PCC. . . . . 18
2.9 One-pot synthesis of chlorolactone ketone 27a. . . . . . . . . 19
2.10 One-pot synthesis of chlorolactone oxime 6a. . . . . . . . . . 21
2.11 The oxidation of secondary alcohols with TCCA, reported by
Dip et al. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
2.12 Oxidation of chlorolactone alcohol 26a with TCCA. . . . . . 22