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).
