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Beilstein J. Org. Chem. 2015, 11, 2521–2539, doi:10.3762/bjoc.11.273
Graphical Abstract
Figure 1: a) Structure of xenicin (1) and b) numbering of the xenicane skeleton according to Schmitz and van ...
Figure 2: Overview of selected Xenia diterpenoids according to the four subclasses [2-20]. The nine-membered carboc...
Figure 3: Representative members of the caryophyllenes, azamilides and Dictyota diterpenes.
Scheme 1: Proposed biosynthesis of Xenia diterpenoids (OPP = pyrophosphate, GGPP = geranylgeranyl pyrophospha...
Scheme 2: Direct synthesis of the nine-membered carbocycle as proposed by Schmitz and van der Helm (E = elect...
Scheme 3: The construction of E- or Z-cyclononenes.
Scheme 4: Total synthesis of racemic β-caryophyllene (22) by Corey.
Scheme 5: Total synthesis of racemic β-caryophyllene (22) by Oishi.
Scheme 6: Total synthesis of coraxeniolide A (10) by Leumann.
Scheme 7: Total synthesis of antheliolide A (18) by Corey.
Scheme 8: a) Synthesis of enantiomer 80, b) total syntheses of coraxeniolide A (10) and c) β-caryophyllene (22...
Scheme 9: Total synthesis of blumiolide C (11) by Altmann.
Scheme 10: Synthesis of a xeniolide F precursor by Hiersemann.
Scheme 11: Synthesis of the xenibellol (15) and the umbellacetal (114) core by Danishefsky.
Scheme 12: Proposed biosynthesis of plumisclerin A (118).
Scheme 13: Synthesis of the tricyclic core structure of plumisclerin A by Yao.
Scheme 14: Total synthesis of 4-hydroxydictyolactone (137) by Williams.
Scheme 15: Photoisomerization of 4-hydroxydictyolactone (137) to 4-hydroxycrenulide (138).
Scheme 16: The total synthesis of (+)-acetoxycrenulide (151) by Paquette.