- Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin
-
Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.
- Donohoe, Timothy J.,Harris, Robert M.,Williams, Oliver,Hargaden, Grainne C.,Burrows, Jeremy,Parker, Jeremy
-
scheme or table
p. 12854 - 12861
(2010/01/29)
-
- Synthesis of the non-adjacent bis-THF core of cis-sylvaticin using a double oxidative cyclisation
-
A short synthesis of the non-adjacent bis-THF core of the Annonaceous acetogenin cis-sylvaticin (1) is described. C2 Symmetrical (Z,E,E,Z)- and (E,E,E,E)-tetraenes 5 and 6 were synthesised in six and three steps respectively from (1E,5E,9E)-cyclododeca-1,5,9-triene. Subsequent permanganate promoted asymmetric bi-directional oxidative cyclisation of tetraene 5 was used to create the non-adjacent bis-THF core of 1, installing seven of the nine stereogenic centres present in the natural product in a single step. Desymmetrisation of the oxidative cyclisation product by mono-tosylation gave access to a C11-C32 fragment of cis-sylvaticin.
- Bhunnoo, Riaz A.,Hobbs, Heather,Laine, Dramane I.,Light, Mark E.,Brown, Richard C. D.
-
scheme or table
p. 1017 - 1024
(2009/05/30)
-
- Total synthesis of cis-solamin: Exploiting the RuO4-catalyzed oxidative cyclization of dienes
-
An enantioselective total synthesis of cis-solamin has been accomplished using a highly diastereoselective ruthenium tetroxide catalyzed oxidative cyclization as a crucial transformation. Further key steps involved an enzymatic desymmetrization, a TPAP-catalyzed oxidative termini differentiation, and a ruthenium-catalyzed Alder-ene reaction. Thus, the total synthesis of cis-solamin was achieved in 11 steps with an overall yield of 7.5%.
- Goeksel, Huelya,Stark, Christian B. W.
-
p. 3433 - 3436
(2007/10/03)
-
- Total synthesis of mucocin
-
The synthesis of the potent antitumor agent, mucocin, 1, was efficiently achieved in 20 steps from cyclodecatriene, thus confirming the proposed structure of this unusual member of the Annonaceous acetogenins. Demonstrating the power of the 'naked' carbon skeleton strategy, all seven asymmetric centers in the key fragment of the molecule were introduced by double AE reaction followed by double AD reaction. Simultaneous two ring closure reactions provided both the THP and THF rings in a single step.
- Neogi, Partha,Doundoulakis, Thomas,Yazbak, Ahmad,Sinha, Santosh C.,Sinha, Subhash C.,Keinan, Ehud
-
p. 11279 - 11284
(2007/10/03)
-