Actin-binding marine macrolides: Total synthesis and biological importance

Angewandte Chemie - International Edition

Volumn 41, Issue 24, 2002, Pages 4632-4653

  Yeung, Kap Sun ^a   Paterson, Ian ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b BRISTOL MYERS SQUIBB PHARMACEUTICAL RESEARCH INSTITUTE   (United States)

Author keywords

Actin; Antitumor agents; Macrolides; Natural products; Total synthesis

Indexed keywords

BIODIVERSITY; METABOLITES; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TUMORS;

BIOLOGICAL IMPORT; MARINE MACROLIDES;

MARINE BIOLOGY;

ACTIN; ANTINEOPLASTIC AGENT; APLYRONINE A; CYTOTOXIC AGENT; MACROLIDE; MYCALOLIDE A; PROTEIN; SCYTOPHYCIN C; SWINHOLIDE A; ULAPUALIDE A; UNCLASSIFIED DRUG;

ANIMAL; ANTINEOPLASTIC ACTIVITY; BIOCHEMISTRY; CANCER CHEMOTHERAPY; CELL FUNCTION; CHEMICAL STRUCTURE; CYTOSKELETON; DIASTEREOISOMER; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; METABOLISM; MOLECULAR PROBE; NONHUMAN; PROTEIN BINDING; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACTINS; ANIMALS; ANTINEOPLASTIC AGENTS; MACROLIDES; MOLECULAR STRUCTURE; PROTEIN BINDING; STEREOISOMERISM;

EID: 0037122039     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290057     Document Type: Review

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64. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
65. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
66. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
67. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
68. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
69. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
70. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
71. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
72. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
73. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
74. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
75. The regioselective macrolactonization of unprotected 1,2-diols in sterically demanding environments has been demonstrated in the construction of the 42-membered macrolactone of the altohyrtins/spongistatins: a) D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747; b) D. A. Evans, B. W. Trotter, P. J. Coleman, B. Côté, L. C. Dias, H. A. Rajapakse, A. N. Tyler, Tetrahedron 1999, 55, 8671-8726; c) J. Guo, K. J. Duffy, K. L. Stevens, P. I. Dalko, R. M. Roth, M. M. Hayward, Y. Kishi, Angew. Chem. 1998, 110, 198-202; Angew. Chem. Int. Ed. 1998, 37, 187-192; d) M. M. Hayward, R. M. Roth, K. J. Duffy, P. I. Dalko, K. L. Stevens, J. Guo, Y. Kishi, Angew. Chem. 1998, 110, 202-206; Angew. Chem. Int. Ed. 1998, 37, 192-196; e) A. B. Smith III, Q. Lin, V. A. Doughty, L. Zhuang, M. D. McBriar, J. K. Kerns, C. S. Brook, N. Murase, K. Nakayama, Angew. Chem. 2001, 113, 202-205; Angew. Chem. Int. Ed. 2001, 40, 196-199; f) I. Paterson, D. Y.-K. Chen, M. J. Coster, J. L. Aceña, J. Bach, K. R. Gibson, L. E. Keown, R. M. Oballa, T. Trieselmann, D. J. Wallace, A. P. Hodgson, R. D. Norcross, Angew. Chem. 2001, 113, 4179-4184; Angew. Chem. Int. Ed. 2001, 40, 4055-4060; g) M. T. Crimmins, J. D. Katz, D. G. Washburn, S. P. Allwein, L. F. McAtee, J. Am. Chem. Soc. 2002, 124, 5661-5663. For an early example of this strategy, as used in the total synthesis of bryostatin, see: M. Kageyama, T. Tamura, M. H. Nantz, J. C. Roberts, P. Somfai, D. C. Whritenour, S. Masamune, J. Am. Chem. Soc. 1990, 112, 7407-7408.
76. a) K. C. Nicolaou, A. P. Patron, K. Ajito, P. K. Richter, H. Khatuya, P. Bertinato, R. A. Miller, M.J. Tomaszewski, Chem. Eur. J. 1996, 2, 847-868;
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80. a) For another total synthesis of preswinholide A, see: K. Nagasawa, I. Shimizu, T. Nakata, Tetrahedron Lett. 1996, 37, 6885-6888; K. Nagasawa, I. Shimizu, T. Nakata, Tetrahedron Lett. 1996, 37, 6881-6884;
81. a) For another total synthesis of preswinholide A, see: K. Nagasawa, I. Shimizu, T. Nakata, Tetrahedron Lett. 1996, 37, 6885-6888; K. Nagasawa, I. Shimizu, T. Nakata, Tetrahedron Lett. 1996, 37, 6881-6884;
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93. a) H. Kigoshi, K. Suenaga, T. Mutou, T. Ishigaki, T. Atsumi, H. Ishiwata, A. Sakakura, T. Ogawa, M. Ojika, K. Yamada, J. Org. Chem. 1996, 61, 5326-5351;
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95. a) H. Kigoshi, K. Suenaga, M. Takagi, A. Akao, K. Kanematsu, N. Kamei, Y. Okugawa, K. Yamada, Tetrahedron 2002, 58, 1075-1102;
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97. a) I. Paterson, C. J. Cowden, M. D. Woodrow, Tetrahedron Lett. 1998, 39, 6037-6040;
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100. Marshall has reported the synthesis of C5-C20 and C21-C34 segments of the aplyronines using chiral allenylindium reagents: J. A. Marshall, B. A. Johns, J. Org. Chem. 2000, 65, 1501-510.
101. a) S. K. Chattopadhyay, J. Kempson, A. McNeil, G. Pattenden, M. Reader, D. E. Rippon, D. Waite, J. Chem. Soc. Perkin Trans. 1 2000, 2415-2428;
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107. c) P. Liu, C. A. Celatka, J. S. Panek, Tetrahedron Lett. 1997, 38, 5445-5448;
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