ChemInform Abstract: Combined Directed Metalation - Cross Coupling Strategies. Total Synthesis of the Aglycones of Gilvocarcin V, M, and E.

ChemInform ◽  
2010 ◽  
Vol 29 (8) ◽  
pp. no-no
Author(s):  
C. A. JAMES ◽  
V. SNIECKUS
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Gilvocarcin V ◽  
Coupling Strategies

ortho and remote metalation – cross coupling strategies. Total synthesis of the naturally occurring fluorenone dengibsinin and the azafluoranthene alkaloid imeluteine

1994 ◽  
Vol 72 (1) ◽  
pp. 227-236 ◽  
Author(s):  
J. -m. Fu ◽  
B. -p. Zhao ◽  
M. J. Sharp ◽  
V. Snieckus
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Dimethyl Ether ◽  
Cross Coupling ◽  
Naturally Occurring ◽  
Ortho Metalation ◽  
Coupling Approach ◽  
Successful Approach ◽  
Coupling Strategies

The total synthesis of the naturally occurring fluorenone, dengibsinin (7a), and the azafluoranthene alkaloid, imeluteine (30e), is described. Using combined ortho metalation – cross coupling sequences that terminate in Friedel–Crafts (18b → 6d) and remote metalation (21a,b → 6c,d) reactions, the synthesis of fluorenone dimethyl ethers 6c and 6d is reported. 6c and 6d were shown not to be identical to dengibsinin dimethyl ether and dengibsin dimethyl ether, respectively, derived from the natural products. This work, together with synthetic and structural evidence from Sargent and Talapatra, led to the reassignment of structures for dengibsinin (7a) and dengibsin (7b). Using the metalation – cross coupling approach, the synthesis of the reassigned dengibsinin (7a) is presented. Two alternate unsuccessful approaches to imeluteine are briefly described (31 + 32 and 33 + 34). The successful approach incorporates the remote metalation – double cyclization, 43 → 44, as the key step.

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

Concise total synthesis of honokiol via Kumada cross coupling

2014 ◽  
Vol 55 (31) ◽  
pp. 4295-4297 ◽  
Author(s):  
Jada Srinivas ◽  
Parvinder Pal Singh ◽  
Yogesh Kumar Varma ◽  
Irfan Hyder ◽  
Halmuthur M. Sampath Kumar
Keyword(s):  
Total Synthesis ◽  
Cross Coupling

Directed Metalation–Suzuki–Miyaura Cross-Coupling Strategies: Regioselective Synthesis of Hydroxylated 1-Methyl-phenanthrenes

2015 ◽  
Vol 80 (19) ◽  
pp. 9410-9424 ◽  
Author(s):  
Kåre B. Jørgensen ◽  
Toni Rantanen ◽  
Thilo Dörfler ◽  
Victor Snieckus
Keyword(s):  
Cross Coupling ◽  
Regioselective Synthesis ◽  
Coupling Strategies

Integrated Pd-catalyzed cross-coupling strategies for furnishing α-carbolines

Tetrahedron ◽  
2017 ◽  
Vol 73 (40) ◽  
pp. 5946-5958 ◽  
Author(s):  
Misayo Sera ◽  
Hideya Mizufune ◽  
Tsuyoshi Ueda ◽  
Masahiro Mineno ◽  
Atsuhiko Zanka
Keyword(s):  
Cross Coupling ◽  
Coupling Strategies

Cross Coupling Strategies towards the Synthesis of the Streptonigrin CD Moiety

Heterocycles ◽  
1999 ◽  
Vol 51 (4) ◽  
pp. 721 ◽  
Author(s):  
Cedric W. Holzapfel ◽  
Renier Crous ◽  
Catherine Dwyer
Keyword(s):  
Cross Coupling ◽  
Coupling Strategies
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