Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Intramolecular Ketalization of Functionalized 7-Norbornenols Leo A. Paquette*, Jeremy D. PettigrewEvans Chemical Laboratories, The Ohio State University, 100 West 18th Avenue, Columbus, OH 43210, USAFax: +1(614)2921685; e-Mail: paquette.1@osu.edu; Recommend Article Abstract Buy Article All articles of this category Abstract Convenient access to polycondensed heterocyclic networks has been realized through exposure of bridged hydroxy acetonides to appropriate reagents. Key words - photochemistry - heterocycles - acetals - sulfones - sulfoxides Full Text References References For reports on efforts towards the synthesis of pseudolaric acid A(1), see: 1a Geng Z. Chen B. Chiu P. Angew. Chem. Int. Ed. 2006, 45: 6197 1b Chen B. Ko RYY. Yuen MSM. Cheng KF. Chiou P. J. Org. Chem. 2003, 68: 495 1c Chiu P. Chen B. Cheng KF. Org. Lett. 2001, 3: 1721 1d Ou L. Hu Y. Song G. Bai D. Tetrahedron 1999, 55: 13999 1e Hu Y. Ou L. Bai D. Tetrahedron Lett. 1999, 40: 545 1f Chiu P. Chen B. Cheng KF. Tetrahedron Lett. 1998, 39: 9229 1g Pan BC. Chang HY. Cai GL. Guo YS. Pure Appl. Chem. 1989, 61: 389 2a Zhou BN. Ying BP. Song GQ. Chen ZX. Han J. Yan YF. Planta Med. 1983, 47: 35 2b Yao JX. Lin XY. Acta Chim. Sin. (Engl. Ed.) 1982, 40: 385 3a Cargill RL. Peet NP. Pond DM. Bundy WA. Sears AB. J. Org. Chem. 1980, 45: 3999 3b Cargill RL. Sears AB. Boehm J. Willcott MR. J. Am. Chem. Soc. 1973, 95: 4346 3c Cargill RL. King TY. Sears AB. J. Org. Chem. 1971, 36: 1423 3d Cargill RL. Sears AB. Willcott MR. J. Am. Chem. Soc. 1970, 92: 6084 3e Cargill RL. Gimare BM. Pond DM. King TY. Sears AB. Willcott MR. J. Am. Chem. Soc. 1970, 92: 3809 4 Basil LF. Nakano H. Frutos R. Kopach M. Meyers AI. Synthesis 2002, 2064 5 Snider BB. Allentoff AJ. Kulkarni YS. J. Org. Chem. 1988, 53: 5320 6a Langer K. Mattay J. J. Org. Chem. 1995, 60: 7256 6b Salomon RG. Coughlin DJ. Ghosh S. Zagorski MG. J. Am. Chem. Soc. 1982, 104: 998 7 More JD. Finney NS. Org. Lett. 2002, 4: 3001 8 Nicolaou KC. Montagnon T. Baran PS. Angew. Chem. Int. Ed. 2002, 41: 1386 9 The use of catalytic Pd(OAc)2 resulted in lower yields. See: Larock RC. Hightower TR. Kraus GA. Hahn P. Zheng D. Tetrahedron Lett. 1995, 36: 2423 10 Rigby JH. Wilson JAZ. J. Org. Chem. 1987, 52: 34 11 This material was found to contain a small amount of the corresponding syn-alcohol (10:1 anti/syn). The assignment of the relative stereochemistry at the newly formed stereogenic center was made on the basis of the ¹H NMR chemical shifts of the signals corresponding to the vinyl and bridgehead protons (anti δ = 5.29/syn δ = 5.55 and anti δ = 2.29/syn δ = 2.38, respectively). See: Clark FRS. Warkentin J. Can. J. Chem. 1971, 49: 2223 For examples of the McMurry reaction used to for polycycles containing seven-membered rings, see 12a Dauben WG. Farkas I. Bridon DP. Chuang CP. Henegar KE. J. Am. Chem. Soc. 1991, 113: 5883 12b Lee E. Yoon CH. Tetrahedron Lett. 1996, 37: 5929 13a Roberts JD. Johnson FO. Carboni RA. J. Am. Chem. Soc. 1954, 76: 5692 13b Winstein S. Shatavsky M. Norton C. Woodward RB. J. Am. Chem. Soc. 1955, 77: 4183 14 For examples of α-sulfonyl sulfones being used in Ramberg-Bäcklund ring contraction reactions, see: Scarpetti D. Fuchs PL. J. Am. Chem. Soc. 1990, 112: 8084 15 Armarego WLF. Perrin DD. Purification of Laboratory Chemicals 4th ed.: Butterworth-Heinemann; Oxford: 1997. 16 Still WC. Kahn M. Mitra A. J. Org. Chem. 1978, 43: 2923 17 Signal disappeared upon the addition of a drop of D2O to the NMR sample.
