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. 2011 Oct 7;67(40):7631-7666.

doi: 10.1016/j.tet.2011.06.079.

Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products

Jon T Njardarson¹

Affiliations

PMID: 23172980
PMCID: PMC3501273
DOI: 10.1016/j.tet.2011.06.079

Synthetic Efforts Toward [3.3.1] Bridged Bicyclic Phloroglucinol Natural Products

Jon T Njardarson. Tetrahedron. 2011.

. 2011 Oct 7;67(40):7631-7666.

doi: 10.1016/j.tet.2011.06.079.

Author

Jon T Njardarson¹

Affiliation

¹ University of Arizona, Department of Chemistry and Biochemistry, 1306 E. University Blvd., Tucson, AZ 85716, USA.

PMID: 23172980
PMCID: PMC3501273
DOI: 10.1016/j.tet.2011.06.079

No abstract available

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Figures

Scheme 1 — Scheme 1
Structures of Hyperforin, Garsubellin A, Nemorosone and Clusianone.

Scheme 2 — Scheme 2
Strategies for construction of the [3.3.1] Bicyclic Core.

Scheme 3 — Scheme 3
K.C. Nicolaou’s 1999 Approach Toward the Garsubellin A Bicyclic Core.

Scheme 4 — Scheme 4
K.C. Nicolaou’s 1999 Synthetic Approach Toward Garsubellin A (Part I).

Scheme 5 — Scheme 5
K.C. Nicolaou’s 1999 Synthetic Approach Toward Garsubellin A (Part II).

Scheme 6 — Scheme 6
K.C. Nicolaou’s 2005 Approach Toward the Hyperforin Bicyclic Core.

Scheme 7 — Scheme 7
K.C. Nicolaou’s 2005 Synthetic Approach Toward Hyperforin.

Scheme 8 — Scheme 8
M. Shibasaki’s 2002 Approach Toward the Garsubellin A Bicyclic Core.

Scheme 9 — Scheme 9
M. Shibasaki’s 2002 Synthetic Approach Toward Garsubellin A (Part 1).

Scheme 10 — Scheme 10
M. Shibasaki’s 2002 Synthetic Approach Toward Garsubellin A (Part 2).

Scheme 11 — Scheme 11
M. Shibasaki’s 2005 Approach Toward Garsubellin A.

Scheme 12 — Scheme 12
M. Shibasaki’s 2005 Total Synthesis of Garsubellin A (Part 1).

Scheme 13 — Scheme 13
M. Shibasaki’s 2005 Total Synthesis of Garsubellin A (Part 2).

Scheme 14 — Scheme 14
M. Shibasaki’s 2007 Approach Toward the Garsubellin A Bicyclic Core.

Scheme 15 — Scheme 15
M. Shibasaki’s 2007 Approach Toward Garsubellin A.

Scheme 16 — Scheme 16
M. Shibasaki’s 2010 Approach Toward Hyperforin.

Scheme 17 — Scheme 17
M. Shibasaki’s 2010 Total Synthesis of ent-Hyperforin (Part 1).

Scheme 18 — Scheme 18
M. Shibasaki’s 2010 Total Synthesis of ent-Hyperforin (Part 2).

Scheme 19 — Scheme 19
M. Shibasaki’s 2010 Total Synthesis of ent-Hyperforin (Part 3).

Scheme 20 — Scheme 20
M. Shibasaki’s 2010 Total Synthesis of ent-Hyperforin (Part 4).

Scheme 21 — Scheme 21
B. M. Stoltz’s 2002 Approach Toward the Garsubellin A Bicyclic Core.

Scheme 22 — Scheme 22
B. M. Stoltz’s 2002 Synthetic Approach Toward Garsubellin A.

Scheme 23 — Scheme 23
David G. J. Young’s 2002 Approach Toward the Garsubellin A Bicyclic Core.

Scheme 24 — Scheme 24
David G. J. Young’s 2002 Synthetic Approach Toward Garsubellin A.

Scheme 25 — Scheme 25
G. A. Kraus’ 2003 Approach Toward the Hyperforin Bicyclic Core.

Scheme 26 — Scheme 26
G. A. Kraus’ 2003 Synthetic Approach Toward Hyperforin.

Scheme 27 — Scheme 27
G. A. Kraus’ 2003 Second Approach Toward the Hyperforin Bicyclic Core.

Scheme 28 — Scheme 28
G. A. Kraus’ 2003 Second Synthetic Approach Toward Hyperforin.

Scheme 29 — Scheme 29
G. A. Kraus’ 2005 Approach Toward the Nemorosone Bicyclic Core.

Scheme 30 — Scheme 30
G. A. Kraus’ 2005 Synthetic Approach Toward Nemorosone.

Scheme 31 — Scheme 31
G. A. Kraus’ 2008 Approach Toward the Papuaforin A Bicyclic Core.

Scheme 32 — Scheme 32
G. A. Kraus’ 2008 Synthetic Approach Toward Papuaforin A.

Scheme 33 — Scheme 33
R. B. Grossman’s 2003 Approach Toward the Nemorosone Bicyclic Core.

Scheme 34 — Scheme 34
R. B. Grossman’s 2003 Synthetic Approach Toward Nemorosone.

Scheme 35 — Scheme 35
G. Mehta’s 2004 Approach Toward the Garsubellin A Bicyclic Core.

Scheme 36 — Scheme 36
G. Mehta’s 2004 Synthetic Approach Toward Garsubellin A (Part 1).

Scheme 37 — Scheme 37
G. Mehta’s 2004 Synthetic Approach Toward Garsubellin A (Part 2).

Scheme 38 — Scheme 38
G. Mehta’s 2006 Approach Toward the Garsubellin A Bicyclic Core.

Scheme 39 — Scheme 39
G. Mehta’s 2006 Synthetic Approach Toward Garsubellin A.

Scheme 40 — Scheme 40
G. Mehta’s 2008 Approach Toward the Guttiferone A Bicyclic Core.

Scheme 41 — Scheme 41
G. Mehta’s 2008 Synthetic Approach Toward Guttiferone A.

Scheme 42 — Scheme 42
G. Mehta’s 2008 Approach Toward the Hyperforin Bicyclic Core.

Scheme 43 — Scheme 43
G. Mehta’s 2008 Synthetic Approach Toward Hyperforin.

Scheme 44 — Scheme 44
G. Mehta’s 2009 Approach Toward the Hyperforin Bicyclic Core.

Scheme 45 — Scheme 45
G. Mehta’s 2009 Synthetic Approach Toward Hyperforin.

Scheme 46 — Scheme 46
G. Mehta’s 2010 Approach Toward the Hyperforin Bicyclic Core.

Scheme 47 — Scheme 47
G. Mehta’s 2010 Synthetic Approach Toward Hyperforin.

Scheme 48 — Scheme 48
R. Takagi’s 2008 Approach Toward the Plukenetione A Bicyclic Core.

Scheme 49 — Scheme 49
R. Takagi’s 2008 Synthetic Approach Toward Plukenetione A.

Scheme 50 — Scheme 50
L. Barriault’s 2005 and 2009 Approaches Toward the Hyperforin Bicyclic Core.

Scheme 51 — Scheme 51
L. Barriault’s 2009 Synthetic Approach Toward Hyperforin.

Scheme 52 — Scheme 52
S. J. Danishefsky’s 2006 Approach Toward Garsubellin A.

Scheme 53 — Scheme 53
S. J. Danishefsky’s 2006 Total Synthesis of Garsubellin A.

Scheme 54 — Scheme 54
S. J. Danishefsky’s 2007 Approach Toward Nemorosone and Clusianone.

Scheme 55 — Scheme 55
S. J. Danishefsky’s 2007 Total Synthesis of Nemorosone.

Scheme 56 — Scheme 56
S. J. Danishefsky’s 2007 Total Synthesis of Clusianone.

Scheme 57 — Scheme 57
N. S. Simpkins’ 2006 Approach Toward Clusianone.

Scheme 58 — Scheme 58
N. S. Simpkins’ 2006 Total Synthesis of Clusianone.

Scheme 59 — Scheme 59
N. S. Simpkins’ 2007 Total Synthesis of (+)-Clusianone.

Scheme 60 — Scheme 60
N. S. Simpkins’ 2007 First Approach Toward Garsubellin A.

Scheme 61 — Scheme 61
N. S. Simpkins’ 2007 Synthetic Approach Toward Garsubellin A.

Scheme 62 — Scheme 62
N. S. Simpkins’ 2007 Second Approach Toward Garsubellin A.

Scheme 63 — Scheme 63
N. S. Simpkins’ 2007 Formal Total Synthesis of Garsubellin A.

Scheme 64 — Scheme 64
N. S. Simpkins’ 2010 Total Synthesis of Nemorosone.

Scheme 65 — Scheme 65
M. Nakada’s 2010 Approach Toward Nemorosone.

Scheme 66 — Scheme 66
M. Nakada’s 2010 Synthetic Approach Toward Nemorosone (Part I).

Scheme 67 — Scheme 67
M. Nakada’s 2010 Synthetic Approach Toward Nemorosone (Part II).

Scheme 68 — Scheme 68
C. Marazano’s 2007 Approach Toward Clusianone.

Scheme 69 — Scheme 69
C. Marazano’s 2006 Total Synthesis of Clusianone.

Scheme 70 — Scheme 70
C. Marazano’s 2007 Second Approach Toward Clusianone.

Scheme 71 — Scheme 71
C. Marazano’s 2007 Second Synthetic Approach Toward Clusianone.

Scheme 72 — Scheme 72
C. Marazano’s 2008 Phloroglucinol Explorations.

Scheme 73 — Scheme 73
J. A. Porco’s, Jr. 2007 Approach Toward Clusianone.

Scheme 74 — Scheme 74
J. A. Porco’s, Jr. 2007 Total Synthesis of Clusianone.

Scheme 75 — Scheme 75
J. A. Porco’s, Jr. 2010 Approach Toward Plukenetione A.

Scheme 76 — Scheme 76
J. A. Porco’s, Jr. 2010 Total Synthesis Plukenetione A.

Scheme 77 — Scheme 77
J. A. Porco’s, Jr. 2010 Total Synthesis of Hyperibone K.

Scheme 78 — Scheme 78
E. A. Couladouros’ 2009 Approach Toward Hyperforin.

Scheme 79 — Scheme 79
E. A. Couladouros 2009 Synthetic Approach Toward Hyperforin.

Scheme 80 — Scheme 80
J. H. George’s 2010 Approach Toward Hyperpapuanone.

Scheme 81 — Scheme 81
J. H. George’s 2010 Synthetic Approach Toward Hyperpapuanone.

Scheme 82 — Scheme 82
D. M. Coltart’s 2010 Approach Toward Clusianone.

Scheme 83 — Scheme 83
D. M. Coltart’s 2010 Total Synthesis of Clusianone.

Scheme 84 — Scheme 84
J. T. Njardarson’s 2011 Approach Toward Guttiferone G.

Scheme 85 — Scheme 85
J. T. Njardarson’s 2011 Synthetic Approach Toward Guttiferone G.

Scheme 86 — Scheme 86
M. Miesch’s 2003 Approach For [3.3.1] Bicyclic Products.

Scheme 87 — Scheme 87
Y. Kuninobu’s 2009 Approach For [3.3.1] Bicyclic Products.

Scheme 88 — Scheme 88
Q. Liu’s 2009 Approach For [3.3.1] Bicyclic Products.

Scheme 89 — Scheme 89
R. Ballini’s 2009 Approach For [3.3.1] Bicyclic Products.

Scheme 90 — Scheme 90
W. E. Crowe’s 2010 Approach For [3.3.1] Bicyclic Products.

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