Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms
- Tatjana Huber,
- Lara Weisheit and
- Thomas Magauer
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.
The chemistry of isoindole natural products
- Klaus Speck and
- Thomas Magauer
Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243
Graphical Abstract
Figure 1: a) Structural features and b) selected examples of non-natural congeners.
Scheme 1: Synthesis of isoindole 18.
Scheme 2: Staining amines with 1,4-diketone 19 (R = H).
Figure 2: Representative members of the indolocarbazole alkaloid family.
Figure 3: Staurosporine (26) bound to the adenosine-binding pocket [19] (from pdb1stc).
Figure 4: Structure of imatinib (34) and midostaurin (35).
Scheme 3: Biosynthesis of staurosporine (26).
Scheme 4: Wood’s synthesis of K-252a via the common intermediate 48.
Scheme 5: Synthesis of 26, 27, 49 and 50 diverging from the common intermediate 48.
Figure 5: Selected members of the cytochalasan alkaloid family.
Scheme 6: Biosynthesis of chaetoglobosin A (57) [56].
Scheme 7: Synthesis of cytochalasin D (70) by Thomas [63].
Scheme 8: Synthesis of L-696,474 (78).
Scheme 9: Synthesis of aldehyde 85 (R = TBDPS).
Scheme 10: Synthesis of (+)-aspergillin PZ (79) by Tanis.
Figure 6: Representative Berberis alkaloids.
Scheme 11: Proposed biosynthetic pathway to chilenine (93).
Scheme 12: Synthesis of magallanesine (97) by Danishefsky [84].
Scheme 13: Kurihara’s synthesis of magallanesine (85).
Scheme 14: Proposed biosynthesis of 113, 117 and 125.
Scheme 15: DNA lesion caused by aristolochic acid I (117) [102].
Scheme 16: Snieckus’ synthesis of piperolactam C (131).
Scheme 17: Synthesis of aristolactam BII (104).
Figure 7: Representative cularine alkaloids.
Scheme 18: Proposed biosynthesis of 136.
Scheme 19: The syntheses of 136 and 137 reported by Castedo and Suau.
Scheme 20: Synthesis of 136 by Couture.
Figure 8: Representative isoindolinone meroterpenoids.
Scheme 21: Postulated biosynthetic pathway for the formation of 156 (adopted from George) [143].
Scheme 22: Synthesis of stachyflin (156) by Katoh [144].
Figure 9: Selected examples of spirodihydrobenzofuranlactams.
Scheme 23: Synthesis of stachybotrylactam I (157).
Scheme 24: Synthesis of pestalachloride A (193) by Schmalz.
Scheme 25: Proposed mechanism for the BF3-catalyzed metal-free carbonyl–olefin metathesis [149].
Scheme 26: Preparation of the isoindoline core of muironolide A (204).
Scheme 27: Proposed biosynthesis of 208.
Scheme 28: Model for the biosynthesis of 215 and 217.
Scheme 29: Synthesis of lactonamycin (215) and lactonamycin Z (217).
Figure 10: Hetisine alkaloids 225–228.
Scheme 30: Biosynthetic proposal for the formation of the hetisine core [167].
Scheme 31: Synthesis of nominine (225).
