Synthesis of Carbohydrate Containing Complex Natural Compounds

12 Synthesis of Carbohydrate Containing Complex Natural Compounds 

Abbreviations Ac, acetyl AIBN, 2,2 -azobisisobutyronitrile All, allyl Alloc, allyloxycarbonyl Bn, benzyl BOM, benzyloxymethyl BPC, p-phenylbenzoyl Bu, butyl t-Bu, tert-butyl Bz, benzoyl CAN, ammonium hexanitratocerate (IV) Cbz, bezyloxycarbonyl CDl, carbonyldiimizazole ClAc, chloroacetyl Cp, cyclopentadienyl CSA, DL-lO-camphorsulfonic acid DABCO, l,4-diazabicyclo[2.2.2]octane DAST, diethylaminosulfur trifluoride dba, dibenzylideneacetone DBU, l,8-diazabicyclo[5.4.0]undec-7-ene DCC, iV,iV-dicyclohexylcarbodiimide DDQ, 2,3-dichloro-5,6-dicyano-l,4-benzoqui-none DEAD, diethyl azodicarboxylate DEIPS, diethylisopropylsilyl DIBAL, diisobutylaluminum hydride DMAP, 

4-dimethylaminopyridine DMA, iV,iV-dimethylacetamide DMF, dimethylfomiamide DNP, dinitrophenyl DTBMP, 2,6-di-fert-butyl-4-methylpyridine Et, ethyl Eu(fod)3, tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium FMOC, 9-fluorenylmethoxycarbonyl HMPA, hexamethyl phosphoric triamide Im, imidazolyl Ipc, isopinocamphenyl IPDMS, isopropyldimethylsilyl KHMDS, potassium bis(trimethylsilyl)amide EAH, lithium aluminum hydride EDA, lithium diisopropylamide EiHMDS, lithium bis(trimethylsilyl)amide mCPBA, m-chloroperoxybenzoic acid Me, methyl MOM, methoxymethyl Ms, methanesulfonyl NB, o-nitrobenzyl NBS, iV-bromosuccinimide NCS, iV-chlorosuccinimide NIS, iV-iodosuccinimide NMO, iV-methylmorpholine iV-oxide NMP, iV-methyl-2-pyrrolidinone PCC, pyridinium chlorochromate Ph, phenyl Phth, phthaloyl PMB, /i-methoxybenzyl Pr, propyl i-Pr, isopropyl PPTS, pyridinium /)-toluenesulfonate Pv, pivaloyl Py, pyridine rt, room temperature TBAP, tetrabutylammonium fluoride TBAI, tetrabutylammonium iodide TBS, tert-butyldimethylsilyl TEOC, 2-(trimethylsilyl)ethoxycarbonyl TES, triethylsilyl Tf, trifluoromethanesulfonyl THE, tetrahydrofuran TIPS, triisopropylsilyl TMEDA, iV,iV,iV, iV -tetramethylethylenediamine TMS, trimethylsilyl TPAP, tetra-n-propylammonium perruthenate Tr, triphenylmethyl TPS, tert-butyldiphenylsilyl Ts, /)-toluenesulfonyl. 

---

The aim of this Report is to review new methodology for the synthesis of saturated heterocyclic compounds. Emphasis is placed on reactions which involve a cyclization step and few ring transformations are described. Heterocycles which contain phosphorus, selenium, and silicon as the heteroatom are omitted. A few key steps in complex natural product syntheses are mentioned, but carbohydrates are excluded. The rapidly increasing numbers of reports describing the synthesis of saturated and unsaturated lactones and of crown ethers are covered in Chapters 3 and 10. 

---