Asymmetric Synthesis of the Epoxide Portion of the Azinomycins

Synlett

Volumn 1996, Issue 10, 1996, Pages 973-974

  Bryant, Helen J ^a   Dardonville, Christophe Y ^a   Hodgkinson, Timothy J ^a,b   Shipman, Michael ^a,b   Slawin, Alexandra M Z ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002109325     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5644     Document Type: Article

References (34)

1. Nagaoka, K.; Matsumoto, M.; Ono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T.; J. Antibiot., 1986, 39, 1527 (isolation); Yokoi, K.; Nagaoka, K.; Nakashima, T.; Chem. Pharm. Bull., 1986, 34, 4554 (characterisation); Ishizeki, S.; Ohtsuka, M.; Irinoda, K.; Kukita, K.-I.; Nagaoka, K.; Nakashima, T.; J. Antibiot., 1987, 40, 60 (anti-tumour activity).
2. Nagaoka, K.; Matsumoto, M.; Ono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T.; J. Antibiot., 1986, 39, 1527 (isolation); Yokoi, K.; Nagaoka, K.; Nakashima, T.; Chem. Pharm. Bull., 1986, 34, 4554 (characterisation); Ishizeki, S.; Ohtsuka, M.; Irinoda, K.; Kukita, K.-I.; Nagaoka, K.; Nakashima, T.; J. Antibiot., 1987, 40, 60 (anti-tumour activity).
3. Nagaoka, K.; Matsumoto, M.; Ono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T.; J. Antibiot., 1986, 39, 1527 (isolation); Yokoi, K.; Nagaoka, K.; Nakashima, T.; Chem. Pharm. Bull., 1986, 34, 4554 (characterisation); Ishizeki, S.; Ohtsuka, M.; Irinoda, K.; Kukita, K.-I.; Nagaoka, K.; Nakashima, T.; J. Antibiot., 1987, 40, 60 (anti-tumour activity).
4. Armstrong, R.W.; Salvati, M.E.; Nguyen, M.; J. Am. Chem. Soc., 1992, 114, 3144.
5. The Anticancer Drugs by Pratt, W.B.; Ruddon, R.W.; Ensminger, W.D.; Maybaum, J.; Oxford University Press, Oxford, 2nd Ed 1994.
6. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
7. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
8. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
9. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
10. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
11. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
12. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
13. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
14. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
15. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
16. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
17. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
18. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
19. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
20. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
21. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
22. For synthetic approaches to the azinomycins, see (a) Shibuya, M.; Terauchi, H.; Tetrahedron Lett., 1987, 28, 2619; (b) Ando, K.; Yamada, T.; Shibuya, M.; Heterocycles, 1989, 29, 2209; (c) England, P.; Chun, K.H.; Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1990, 31, 2669; (d) Moran, E.J.; Armstrong, R.W.; Tetrahedron Lett., 1991, 32 3807; (e) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; J. Org. Chem.; 1992, 57, 2208; (f) Shishido, K.; Omodani, T.; Shibuya, M.; J. Chem. Soc., Perkin Trans. 1; 1992, 2053; (g) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1992, 57, 5813; (h) Armstrong, R.W.; Moran, E.J.; J. Am. Chem. Soc., 1992, 114, 371; (i) Hashimoto, M.; Yamada, K.; Terashima, S.; Chem. Lett., 1992, 975; (j) Armstrong, R.W.; Tellew, J.E.; Zhao, Z.; Moran, E.J.; J. Org. Chem.; 1993, 58, 7848; (k) Coleman, R.S.; Carpenter, A.J.; J. Org. Chem., 1993, 58, 4452; (l) Konda, Y.; Machida, T.; Sasaki, T.; Takeda, K.; Takayanagi, H.; Harigaya, Y.; Chem. Pharm. Bull., 1994, 42, 285; (m) Hashimoto, M.; Terashima, S.; Chem. Lett., 1994, 1001; (n) Hashimoto, M.; Matsumoto, M.; Yamada, K.; Terashima, S.; Tetrahedron Lett., 1994, 35, 2207; (o) Hashimoto, M.; Terashima, S.; Tetrahedron Lett., 1994, 35, 9409; (p) Armstrong, R.W.; Tellew, J.E.; Moran, E.J.; Tetrahedron Lett; 1996, 37, 447; (q) Konda, Y.; Machida, T.; Akaiwa, M., Takeda, K.; Harigaya, Y.; Heterocycles, 1996, 43, 555.
23. Kolb, H.C.; VanNieuwenhze, M.S.; Sharpless, K.B.; Chem. Rev., 1994, 94, 2483.
24. Lhommet, G.; Richaud, M.G.; Maitte, P.; C.R. Seances Acad. Sci., Ser C, 1980, 290, 445.
25. All new compounds have been fully characterised using standard spectroscopic and analytical techniques.
26. 3 to buffer asymmetric dihydroxylation reactions involving base sensitive substrates has been described elsewhere (see ref 6).
27. During the completion of this work, a paper describing the asymmetric dihydroxylation of benzyl 3,3-dimethylacrylate with AD-mix-β appeared in the literature (Shao H.; Goodman, M.; J. Org. Chem.; 1996, 61, 2582).
28. -1) revealed that it was a 98:2 ratio of enantiomers [14.3 min (major); 17.3 min (minor)]. The corresponding racemic material was prepared and used as a standard in this analysis.
29. The refined atomic co-ordinates for this structure have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
30. -1) revealed that it was ≥95%ee [26.4 min (major); 28.9 min (minor)]. The corresponding (R)-enantiomer was prepared using AD-mix-β and used as a standard in this analysis.
31. Koch, P.; Nakatani, Y.; Luu, B.; Ourisson, G; Bull. Soc. Chim. Fr.; 1983, 189. We are unable to account for the discrepancy in the magnitude of these rotations since we have established that no racemisation occurs during the conversion of (A)-4 into (S)-8.
32. 3).
33. D +11.5 (c 1.9, EtOH) for (2S,3S)-1. We correct the optical rotation originally reported for this material by Ando et al (ref 5b). The optical rotation of a related structure in this paper has already been revised (see ref 5f).
34. 3. (2R,3R)-1 was used as a standard for comparison purposes in this analysis. Integration of the methyl resonances at δ1.26 [(2R,3R)-1] and δ1.25 [(2S,3S)-1] revealed an enantiomeric excess ≥95% for (2S,3S)-1.