Free accessResearch articleFirst published online 2013-7
Use of RCM Reactions for Construction of Eight-Membered Carbocycles and Introduction of a Hydroxy Group at the Juncture between Five- and Eight-Membered Carbocycles
Model studies for total synthesis of YW3699 were carried out in order to introduce a hydroxy group at the ring juncture between 5- and 8-membered carbocycles. The five-membered ring part hydrazone and aldehyde with a cyclohexane ring were connected by the Shapiro reaction followed by conversion to diketones which were treated with IBX to afford hydroxylated models.
WangY, DreyfussM, PonelleM, ObererL, RiezmanH., (1998) A glycosylphosphatidylinositol-anchoring inhibitor with an unusual tetracarbocyclic sesterterpene skeleton from the fungus Codinaea simplex. Tetrahedron, 54, 6415–6426.
2.
WangY, ObererL, DreyfussM, SütterlinC, RiezmanH. (1998) Conformation and relative configuration of a very potent glycosylphosphatidylinositol-anchoring inhibitor with an unusual tricarbocyclic sesterterpenoid δ-lactone skeleton from the fungus Paecilomyces inflatus, Helvetica Chimica Acta, 81, 2031–2042.
3.
SütterlinC, HorvathA, GeroldP, SchwarzRT, WangY, DreyfussM, RiezmanH. (1997) Identification of a species-specific inhibitor of glycosylphosphatidylinositol synthesis. The EMBO Journal, 16, 6374–6383.
4.
MizutaniR, NakashimaK, SaitoY, SonoM, ToriM., (2009) Studies toward the total synthesis of YW3699, a sesterterpenoid GPI biosynthesis inhibitor: preparation of the tri-substituted cyclooctene ring using the RCM reaction. Tetrahedron Letters, 50, 2225–2227.
5.
MizutaniR, MikiT, NakashimaK, SaitoY, SonoM, ToriM., (2009) Trisubstituted double bond in the cyclooctene ring. Preparation using the RCM reaction. Heterocycles, 78, 2295–2314.
6.
ToriM, MizutaniR., (2010) Construction of eight-membered carbocycles with trisubstituted double bonds using ring closing metathesis reaction. Molecules, 15, 4242–4260.
7.
DuschekA, KirschSF. (2009) Novel oxygenations with IBX. Chemistry a European Journal, 15, 10713–10717.
8.
VedejsE, EnglerDA, TelschowJE. (1978) Transition-metal peroxide reactions. Synthesis of α-hydroxycarbonyl compounds from enolates. The Journal of Organic Chemistry, 43, 188–196.
9.
LinHY, CauseyR, GarciaGE, SniderBB. (2012) Synthesis of (±)-7-hydroxylycopodine, The Journal of Organic Chemistry, 77, 7143–7156.
10.
TrzossJ, XuJ, LacoskeMH, MobleyWC, TheodorakisEM. (2011) Enantioselective synthesis of (-)-jiadifenin, a potent neurotrophic modulator, Organic Letters, 13, 4554–4557.
11.
SheldrickGM. (1997) SHELXL-97. Program Crystal Structure Refinement. University of Göttingen, Germany.
12.
SheldrickGM. (2008) A short histry of SHELX, Acta Crystallographica Section AA64, 112–122.