Short New Route to the Chiral Spiro‐Tetrahydrofuran Subunit Common to Some Terpenoids

References

• Ina , K. , Sakato , Y. and Fukami , H. 1968 . Isolation and structure elucidation of theaspirone . Tetrahedron Lett. , : 2777
   Google Scholar
• Schulte‐Elte , K. H. , Gautschi , F. , Renold , W. , Hauser , A. , Fankhanser , P. , Limacher , J. and Ohloff , G. 1978 . Vitispiranes, important constituents of vanilla aroma . Helv. Chim. Acta. , 61 : 1125
   Web of Science ®Google Scholar
• Schmitz , F. J. and McDonald , F. J. 1974 . Marine natural products: Sesquiterpene alcohols and ethers from the sea hare Aplysia dactyloanela . Tetrahedron Lett. , : 2541
   Google Scholar
• Schmitz , F. J. , McDonald , F. J. and Vanderah , D. 1978 . Marine natural products: Dactyloxene‐B, a sesquiterpene ether from the sea hare Aplysia dactyloanela . J. Org. Chem. , 43 : 4220
   Google Scholar
• Backvall , J.‐E. and Andersson , P. G. 1991 . Stereocontrolled oxaspirocyclization of conjugated dienes via palladium catalysis . J. Org. Chem. , 56 : 2274
   Google Scholar
• Young , J.‐J. , Jung , L.‐J. and Cheng , K.‐M. 2000 . Amberlyst‐15‐catalyzed intramolecular SN2′ oxaspirocyclization of secondary alcohols. Application to the total synthesis of spirocyclic ethers theaspirane and theaspirone . Tetrahedron Lett. , 41 : 3415
   Web of Science ®Google Scholar
• Schulte‐Elte , K. H. , Umiker , T. and Ohloff , G. 1980 . Synthesis of spirocyclic tetrahydrofuran derivatives of monocyclonerdidol . Helv. Chim. Acta , 63 : 284
   Google Scholar
• Weyerstahl , P. , Buchmann , B. and Marschall‐Weyerstahl , H. 1988 . Syntheses und olfaktorische eigenschaften von theaspiran‐analoga . Leibigs Ann. Chem. , : 507
   Google Scholar
• Paquette , L. A. , Lanter , J. C. and Wang , H.‐L. 1996 . Concise synthesis of cis‐ and trans‐ theaspirones via oxonium ion‐initiated pinacol ring expansion . J. Org. Chem. , 61 : 1119
   Web of Science ®Google Scholar
• Mehta , G. , Chattopadhyay , S. K. and Umarya , J. D. 1999 . A new carvone based construction of the ring‐A of taxoids . Tetrahedron Lett. , 40 : 4881
   Google Scholar
• Mehta , G. , Karmakar , S. and Chattopadhyay , S. K. 2004 . Grob‐type fragmentation of a carvone‐derived β‐hydroxymesylate: Application to the synthesis of chiral lavandulol derivatives . Tetrahedron , 60 : 5013
   Google Scholar
• McChesney , J. D. and Thompson , T. N. 1985 . Stereochemistry of the reductive alkylation of α,β‐epoxy ketones . J. Org. Chem. , 50 : 3473
   Google Scholar
• Meulemans , T. M. , Stork , G. A. , Jansen , B. J. M. and de Groot , A. 1998 . Enantioselective synthesis of highly functionalised cyclohexanones . Tetrahedron Lett. , 39 : 6565
   Google Scholar
• Harding , K. E. and Tiner , T. H. 1991 . Comprehensive Organic Synthesis Edited by: Trost , B. M. and Fleming , I. Vol. 4 , 363 Oxford : Pergamon Press .
   Google Scholar
• Rousseau , G. and Robin , S. 1998 . Electrophilic cyclization of unsaturated amides . Tetrahedron , 54 : 13681
   Web of Science ®Google Scholar
• Haas , J. , Piguel , S. and Wirth , T. 2002 . Reagent‐controlled stereoselective iodolactonization . Org. Lett. , 4 : 297
   PubMed Web of Science ®Google Scholar
• Bew , S. P. , Barks , J. M. , Knight , D. W. and Middleton , R. J. 2000 . Stereochemical features of iodocyclisations of 3‐alkene‐1,2‐diols to β‐hydroxytetrahydrofurans . Tetrahedron Lett. , 41 : 4447
   Google Scholar
• Tamaru , Y. , Hojo , M. , Kawamura , S. , Sawada , S. and Yoshida , Z. 1987 . Stereoselective intramolecular iodoetherification of 4‐pentene‐1,3‐diols: Synthesis of cis‐2‐(iodomethyl)‐3‐hydroxytetrahydrofurans . J. Org. Chem. , 52 : 4062
   Web of Science ®Google Scholar
• Bongini , A. , Cardillo , G. , Orema , M. , Porzi , G. and Sandri , S. 1987 . A new synthesis of both the enantiomers of 4‐amino‐3‐hydroxybutanoic acid (gabob) and MM2 calculations for rotamers of the intermediate oxazolidin‐2‐one . Tetrahedron , 43 : 4377
   Web of Science ®Google Scholar
• Srikrishna , A. and Dethe , D. H. 2004 . Synthetic approaches to guanacastepenes. Enantiospecific syntheses of BC and AB ring systems of guanacastapenes and rameswaralide . Org. Lett. , 6 : 165 – 168 . For some recent reports on the utility of carvone in natural product synthesis, see
   Google Scholar
• Srikrishna , A. , Ravi Kumar , P. and Ramasastry , S. S.V. 2004 . Carbanion cyclisation of esters. Part 2: Enantiospecific construction of the tricyclic framework of the marine sesquiterpenes, spirodysins . Tetrahedron Lett. , 45 : 383 – 386 .
   Google Scholar
• Mehta , G. and Senthilkumaran , R. 2003 . A general, ring‐closure metathesis based enantiospecific approach to polyfunctional eudesmane, ermophilane and agarofuran sesquiterpenoids . Tetrahedron Lett. , 44 : 7055 – 7059 .
   Google Scholar
• Nicolaou , K. C. , Xu , J.‐Y. , Kim , S. , Ohshima , T. , Hosokawa , S. and Pfefferkorn , J. 1997 . Synthesis of the tricyclic core of elutherobin and sarcodictyins and total synthesis of sarcodictyin A . J. Am. Chem. Soc. , 119 : 11353 – 11354 .
   Google Scholar