- Stereoselective synthesis of (-) - Pironetin by an iterative prins cyclisation and reductive cleavage strategy
-
A stereoselective synthesis of pironetin, a natural product which is highly immunosuppressive and shows remarkable plant growth regulatory and antitumoral activities, is described. The approach avails successfully the high stereoselection of Prins cyclisation. The route relies, in addition, on the reductive opening of cyclic ethers, olefin metathesis, and lithium acetylide displacement of tosylate. Georg Thieme Verlag Stuttgart.
- Yadav,Ather, Hissana,Rao, N. Venkateswar,Reddy, M. Sridhar,Prasad
-
scheme or table
p. 1205 - 1208
(2010/08/05)
-
- One-pot hydrosilylation-RCM-protodesilylation: Application to the synthesis of ω-alkenyl α,β-unsaturated lactones
-
A simple and efficient one-pot procedure has been developed for the synthesis of α,β-unsaturated lactones bearing a pendant E-olefin. This new methodology, which features a hydrosilylation, a ring-closing metathesis (RCM) and a protodesilylation reaction,
- Bressy, Cyril,Bargiggia, Frédéric,Guyonnet, Mathieu,Arseniyadis, Stellios,Cossy, Janine
-
body text
p. 565 - 568
(2009/07/10)
-
- Asymmetric total synthesis of the immunosuppressant (-)-pironetin
-
(Chemical Equation Presented) A short, enantioselective total synthesis of the title compound 1 is described. The 14-step synthesis features a highly stereoselective Brown-type pentenylation and a onepot hydrosilylation/ring- closing metathesis (RCM)/prot
- Bressy, Cyril,Vors, Jean-Pierre,Hillebrand, Stefan,Arseniyadis, Stellios,Cossy, Janine
-
scheme or table
p. 10137 - 10140
(2009/05/30)
-
- Asymmetric total synthesis of (-)-pironetin employing the SAMP/RAMP hydrazone methodology
-
A convergent asymmetric total synthesis of pironetin (1), a polyketide with immunosuppressive, antitumor, and plant-growth regulating activities is described. The synthesis was realized by coupling between the C 8-C14 2 and C7/
- Enders, Dieter,Dhulut, Sylvie,Steinbusch, Daniel,Herrbach, Audrey
-
p. 3942 - 3949
(2008/02/08)
-
- Catalytic asymmetric assembly of stereodefined propionate units: An enantioselective total synthesis of (-)-pironetin
-
Double diastereoselection in alkaloid-catalyzed acyl halide-aldehyde cyclocondensation (AAC) reactions provides a strategy for realizing syn- or anti-selective propionate aldol additions from a common reaction manifold. Matched AAC homologation of enantio
- Shen, Xiaoqiang,Wasmuth, Andrew S.,Zhao, Junping,Zhu, Cheng,Nelson, Scott G.
-
p. 7438 - 7439
(2007/10/03)
-
- Total synthesis of the immunosupressant (-)-pironetin (PA48153C).
-
[reaction: see text]. Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned. Key steps include a diastereoselective Lewi
- Keck,Knutson,Wiles
-
p. 707 - 710
(2007/10/03)
-
- An efficient synthesis of pironetins employing a useful chiral building block, (1S, 5S, 6R)-5-hydroxybicyclo [4.1.0]heptan-2-one
-
A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (IS, 5S, 6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated.
- Watanabe, Hidenori,Watanabe, Hiroyuki,Bando, Masahiko,Kido, Masaru,Kitahara, Takeshi
-
p. 9755 - 9776
(2007/10/03)
-
- Total synthesis of (-)-pironetin
-
The convergent total synthesis of (-)-pironetin using a chiral building block, (1S, 5S, 6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 4 and the epoxide 2 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 15, which was converted to pironetin 1 in a few steps.
- Watanabe, Hiroyuki,Watanabe, Hidenori,Kitahara, Takeshi
-
p. 8313 - 8316
(2007/10/03)
-
- Total synthesis of (-)-PA-48153C (pironetin) utilising L-quebrachitol as a chiral building block
-
The chiral and stereoselective synthesis of (-)-PA-48153C (pironetin) 1, a novel immunosuppressant, is described; the acyclic portion possessing four contiguous chiral centres in 1 was constructed stereoselectively from L-quebrachitol and the 2-pyranone m
- Chida, Noritaka,Yoshinaga, Mitsukane,Tobe, Takahiko,Ogawa, Seiichiro
-
p. 1043 - 1044
(2007/10/03)
-
- Total Synthesis of (-)-PA-48153C, a Novel Immunosuppressive 2-Pyranone Derivative
-
(-)-PA-48153C (1), an immunosuppressive agent, was synthesized by starting from (+)-methyl 4,6-O-benzylidene-α-D-glucopyranoside (2) and (S)-(+)-methyl 3-hydroxy-2-methylpropionate (3).The key steps in this synthesis relied upon trans-diaxial ring opening of epoxy mesylate 11 in order to introduce the C-5β ethyl group, Wittig reaction of aldehyde 15 with a phosphorus ylide derived from phosphonium salt 28 to combine the cyclic segment B and the acyclic segment C, and regio- and stereoselective hydroboration of (Z)-olefin 29 in order to introduce the C-8α hydroxyl group.The absolute stereochemistry of PA-48153C was unambiguously determined to be the same as that of 1.
- Yasui, Ken,Tamura, Yoshinori,Nakatani, Takuji,Kawada, Kenji,Ohtani, Mitsuaki
-
p. 7567 - 7574
(2007/10/03)
-