Preparation of optically active diol derivatives by the enzymatic hydrolysis of cyclic carbonates

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 10, 1996, Pages 2977-2987

  Matsumoto, Kazutsugu ^a   Fuwa, Seiji ^a   Shimojo, Megumi ^a   Kitajima, Hidehiko ^a  

^a UNIVERSITY OF FUKUI   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001331078     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.2977     Document Type: Article

References (41)

1. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
2. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
3. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
4. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
5. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
6. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
7. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
8. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
9. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
10. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
11. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
12. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
13. For recent examples, see: a) R. L. Pederson, K. K.-C. Liu, J. F. Rutan, L. Chen,and C.-H. Wong, J. Org. Chem., 55, 4897 (1990); b) M.-J. Kim, and Y. K. Choi, J. Org. Chem., 57, 1605 (1992); c) S. Matsumura, H. Imafuku, Y. Takahashi, and K. Toshima, Chem. Lett., 1993, 251; d) K. Matsumoto, M. Shimagaki, T. Nakata, and T. Oishi, Tetrahedron Lett., 34, 4935 (1993); e) X. J. Chen, A. Archelas, and R. Furstoss, J. Org. Chem., 58, 5528 (1993); f) N. W. Boaz and R. L. Zimmerman, Tetrahedron: Asymmetry, 5, 153 (1994); g) M. Pallavicini, E. Valoti, L. Villa, and O. Piccolo, J. Org. Chem., 59, 1751 (1994); h) H. J. M. Gijsen and C.-H. Wong, J. Am. Chem. Soc., 117, 7585 (1995); i) T. Hudlicky, M. A. A. Endoma, and G. Butora, Tetrahedron: Asymmetry, 7, 61 (1996); j) K. Nakamura, S. Kondo, Y. Kawai, K. Hida, K. Kitano, and A. Ohno, Tetrahedron: Asymmetry, 7, 409 (1996); k) R. Duncan and D. G. Drueckhammer, J. Org. Chem., 61, 438 (1996); l) R. Chênevert and M. Desjardins, J. Org. Chem., 61, 1219 (1996); m) S. Pedragosa-Moreau, A. Archelas, and R. Furstoss, Tetrahedron, 52, 4593 (1996).
14. For recent examples, see: a) D. Bianchi, A. Bosetti, P. Cesti, and P. Golini, Tetrahedron Lett., 33, 3231 (1992); b) L. Poppe, L. Novák, M. Kajtár-Peredy, and C. Szántay, Tetrahedron: Asymmetry, 4, 2211 (1993); c) C. Bonini, R. Racioppi, L. Viggiani, G. Righi, and L. Rossi, Tetrahedron: Asymmetry, 4, 793 (1993); d) C. R. Johnson and M. W. Miller, J. Org. Chem., 60, 6674 (1995).
15. For recent examples, see: a) D. Bianchi, A. Bosetti, P. Cesti, and P. Golini, Tetrahedron Lett., 33, 3231 (1992); b) L. Poppe, L. Novák, M. Kajtár-Peredy, and C. Szántay, Tetrahedron: Asymmetry, 4, 2211 (1993); c) C. Bonini, R. Racioppi, L. Viggiani, G. Righi, and L. Rossi, Tetrahedron: Asymmetry, 4, 793 (1993); d) C. R. Johnson and M. W. Miller, J. Org. Chem., 60, 6674 (1995).
16. For recent examples, see: a) D. Bianchi, A. Bosetti, P. Cesti, and P. Golini, Tetrahedron Lett., 33, 3231 (1992); b) L. Poppe, L. Novák, M. Kajtár-Peredy, and C. Szántay, Tetrahedron: Asymmetry, 4, 2211 (1993); c) C. Bonini, R. Racioppi, L. Viggiani, G. Righi, and L. Rossi, Tetrahedron: Asymmetry, 4, 793 (1993); d) C. R. Johnson and M. W. Miller, J. Org. Chem., 60, 6674 (1995).
17. For recent examples, see: a) D. Bianchi, A. Bosetti, P. Cesti, and P. Golini, Tetrahedron Lett., 33, 3231 (1992); b) L. Poppe, L. Novák, M. Kajtár-Peredy, and C. Szántay, Tetrahedron: Asymmetry, 4, 2211 (1993); c) C. Bonini, R. Racioppi, L. Viggiani, G. Righi, and L. Rossi, Tetrahedron: Asymmetry, 4, 793 (1993); d) C. R. Johnson and M. W. Miller, J. Org. Chem., 60, 6674 (1995).
18. For recent examples, see: a) B. Herradón, S. Cueto, A. Morcuende, and S. Valverde, Tetrahedron: Asymmetry, 4, 845 (1993); b) A. Mattson, N. Öhrner, K. Hult, and T. Norin, Tetrahedron: Asymmetry, 4, 925 (1993); c) H. Nagai, T. Morimoto, and K. Achiwa, Synlett, 1994, 289; d) F. Theil, J. Weidner, S. Ballschuh, A. Kunath, and H. Schick, J. Org. Chem., 59, 388 (1994); e) S. Fernández, F. Ferrero, V. Gotor, and W. H. Okamura, J. Org. Chem., 60, 6674 (1995).
19. For recent examples, see: a) B. Herradón, S. Cueto, A. Morcuende, and S. Valverde, Tetrahedron: Asymmetry, 4, 845 (1993); b) A. Mattson, N. Öhrner, K. Hult, and T. Norin, Tetrahedron: Asymmetry, 4, 925 (1993); c) H. Nagai, T. Morimoto, and K. Achiwa, Synlett, 1994, 289; d) F. Theil, J. Weidner, S. Ballschuh, A. Kunath, and H. Schick, J. Org. Chem., 59, 388 (1994); e) S. Fernández, F. Ferrero, V. Gotor, and W. H. Okamura, J. Org. Chem., 60, 6674 (1995).
20. For recent examples, see: a) B. Herradón, S. Cueto, A. Morcuende, and S. Valverde, Tetrahedron: Asymmetry, 4, 845 (1993); b) A. Mattson, N. Öhrner, K. Hult, and T. Norin, Tetrahedron: Asymmetry, 4, 925 (1993); c) H. Nagai, T. Morimoto, and K. Achiwa, Synlett, 1994, 289; d) F. Theil, J. Weidner, S. Ballschuh, A. Kunath, and H. Schick, J. Org. Chem., 59, 388 (1994); e) S. Fernández, F. Ferrero, V. Gotor, and W. H. Okamura, J. Org. Chem., 60, 6674 (1995).
21. For recent examples, see: a) B. Herradón, S. Cueto, A. Morcuende, and S. Valverde, Tetrahedron: Asymmetry, 4, 845 (1993); b) A. Mattson, N. Öhrner, K. Hult, and T. Norin, Tetrahedron: Asymmetry, 4, 925 (1993); c) H. Nagai, T. Morimoto, and K. Achiwa, Synlett, 1994, 289; d) F. Theil, J. Weidner, S. Ballschuh, A. Kunath, and H. Schick, J. Org. Chem., 59, 388 (1994); e) S. Fernández, F. Ferrero, V. Gotor, and W. H. Okamura, J. Org. Chem., 60, 6674 (1995).
22. For recent examples, see: a) B. Herradón, S. Cueto, A. Morcuende, and S. Valverde, Tetrahedron: Asymmetry, 4, 845 (1993); b) A. Mattson, N. Öhrner, K. Hult, and T. Norin, Tetrahedron: Asymmetry, 4, 925 (1993); c) H. Nagai, T. Morimoto, and K. Achiwa, Synlett, 1994, 289; d) F. Theil, J. Weidner, S. Ballschuh, A. Kunath, and H. Schick, J. Org. Chem., 59, 388 (1994); e) S. Fernández, F. Ferrero, V. Gotor, and W. H. Okamura, J. Org. Chem., 60, 6674 (1995).
23. a) R. A. Holton, C. Somoza, H.-B. Kim, F. Liang, R. J. Biediger, D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K. K. Murthi, L. N. Gentile, and J. H. Liu, J. Am. Chem. Soc., 116, 1597 (1994); R. A. Holton, H.-B. Kim, C. Somoza, F. Liang, R. J. Biediger, D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K. K. Murthi, L. N. Gentile, and J. H. Liu, J. Am. Chem. Soc., 116, 1599 (1994);
24. a) R. A. Holton, C. Somoza, H.-B. Kim, F. Liang, R. J. Biediger, D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K. K. Murthi, L. N. Gentile, and J. H. Liu, J. Am. Chem. Soc., 116, 1597 (1994); R. A. Holton, H.-B. Kim, C. Somoza, F. Liang, R. J. Biediger, D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K. K. Murthi, L. N. Gentile, and J. H. Liu, J. Am. Chem. Soc., 116, 1599 (1994);
25. b) K. C. Nicolaou, Z. Yang, J. J. Liu, H. Ueno, P. G. Nanterment, R. K. Guy, C. F. Claiborne, J. Renaud, E. A. Couladourous, K. Paulvannan, and E. J. Sorensen, Nature, 367, 630 (1994).
26. a) C. Y. Hong and Y. Kishi, J. Org. Chem., 55, 4242 (1990);
27. b) T. Nakata, H. Matsukura, D. Jian, and H. Nagashima, Tetrahedron Lett., 35, 8229 (1994).
28. A. preliminary report of this reaction: K. Matsumoto, S. Fuwa, and H. Kitajima, Tetrahedron Lett., 36, 6499 (1995).
29. a) R. M. Burk and M. B. Roof, Tetrahedron Lett., 34, 395 (1993);
30. b) N. N. Bhongle and J. Y. Tang, Tetrahedron Lett., 36, 6803 (1995).
31. C.-S. Chen, Y. Fujimoto, G. Girdaukas, and C. J. Sih, J. Am. Chem. Soc., 104, 7294 (1982).
32. K.-C. Tang, B. E. Tropp, and R. Engel, Tetrahedron, 34, 2873 (1978).
33. P. G. Hultin and J. B. Jones, Tetrahedron Lett., 33, 1399 (1992).
34. L. Sarda and P. Desnuelle, Biochim. Biophys. Acta, 30, 513 (1958).
35. C. Laane, S. Boeren, K. Vos, and C. Veeger, Biotechnol. Bioeng., 30, 81 (1987).
36. W. L. Nelson, J. E. Wennerstrom, and S. R. Sankar, J. Org. Chem., 42, 1006 (1977).
37. a) E. Baer and H. O. L. Fischer, J. Biol. Chem., 128, 463 (1939);
38. b) J. J. Baldwin, A. W. Raabo, K. Mensler, B. H. Arison, and D. E. McClure, J. Org. Chem., 43, 4876 (1978).
39. Y. Masaoka, M. Sakakibara, and K. Mori, Agric. Biol. Chem., 46, 2319 (1982).
40. F. Theil, J. Weinder, S. Ballschuh, A. Kunath, and H. Schick, J. Org. Chem., 59, 388 (1994).
41. J. Mulzer and P. D. Lasalle, J. Chem. Res., (S), 1983, 10.