Synthesis of benzofurans through coupling of dienylacetylenes with carbene complexes: Total synthesis of egonol

Tetrahedron

Volumn 59, Issue 29, 2003, Pages 5609-5616

  Zhang, Jianwei ^a   Zhang, Yi ^a   Zhang, Yanshi ^a   Herndon, James W ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

Benzofuran; Carbene complexes; Conjugated alkynes; Sonogashira coupling

Indexed keywords

ACETYLENE DERIVATIVE; BENZOFURAN DERIVATIVE; CARBENOID; EGONOL; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; SILYLATION;

EID: 0037707402     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00823-8     Document Type: Article

References (55)

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2. (a) Jackson T.J., Herndon J.W. Tetrahedron. 57:2001;3859-3868 (b) Herndon J.W., Zhang Y., Wang H., Wang K. Tetrahedron Lett. 41:2000;8687-8690 (c) Herndon J.W., Hayford A. Organometallics. 14:1995;1556-1558 (d) Herndon J.W., Wang H. J. Org. Chem. 63:1998;4562-4563 (e) Zhang Y., Herndon J.W. Tetrahedron. 56:2000;2175-2184 (f) Waters M.L., Bos M.E., Wulff W.D. J. Am. Chem. Soc. 121:1999;6403-6413.
3. (a) Jackson T.J., Herndon J.W. Tetrahedron. 57:2001;3859-3868 (b) Herndon J.W., Zhang Y., Wang H., Wang K. Tetrahedron Lett. 41:2000;8687-8690 (c) Herndon J.W., Hayford A. Organometallics. 14:1995;1556-1558 (d) Herndon J.W., Wang H. J. Org. Chem. 63:1998;4562-4563 (e) Zhang Y., Herndon J.W. Tetrahedron. 56:2000;2175-2184 (f) Waters M.L., Bos M.E., Wulff W.D. J. Am. Chem. Soc. 121:1999;6403-6413.
4. (a) Jackson T.J., Herndon J.W. Tetrahedron. 57:2001;3859-3868 (b) Herndon J.W., Zhang Y., Wang H., Wang K. Tetrahedron Lett. 41:2000;8687-8690 (c) Herndon J.W., Hayford A. Organometallics. 14:1995;1556-1558 (d) Herndon J.W., Wang H. J. Org. Chem. 63:1998;4562-4563 (e) Zhang Y., Herndon J.W. Tetrahedron. 56:2000;2175-2184 (f) Waters M.L., Bos M.E., Wulff W.D. J. Am. Chem. Soc. 121:1999;6403-6413.
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11. For recent examples, see: (a) Cacchi S., Fabrizi G., Goggiomani A. Heterocycles. 56:2002;613-632 (b) Panda A.K., Parthasarathy M.R. Indian J. Chem. Sect. B. 2001;628-631 (c) Hu Y., Yang Z. Org. Lett. 3:2001;1387-1390 (d) Frackenpohl J., Braje W.M., Hoffmann H.M.R. J. Chem. Soc., Perkin Trans. 1. 2001;47-65 (e) Hiroya K., Suzuki N., Yasuhara A., Egawa Y., Kasano A., Sakamoto T. J. Chem. Soc., Perkin Trans. 1. 2000;4339-4346. A similar reaction using internal alkynes proceeding through an alkyne insertion mechanism has also been employed Larock R.C., Doty M.J., Han X. Tetrahedron Lett. 39:1998;5143-5146.
12. For recent examples, see: (a) Cacchi S., Fabrizi G., Goggiomani A. Heterocycles. 56:2002;613-632 (b) Panda A.K., Parthasarathy M.R. Indian J. Chem. Sect. B. 2001;628-631 (c) Hu Y., Yang Z. Org. Lett. 3:2001;1387-1390 (d) Frackenpohl J., Braje W.M., Hoffmann H.M.R. J. Chem. Soc., Perkin Trans. 1. 2001;47-65 (e) Hiroya K., Suzuki N., Yasuhara A., Egawa Y., Kasano A., Sakamoto T. J. Chem. Soc., Perkin Trans. 1. 2000;4339-4346. A similar reaction using internal alkynes proceeding through an alkyne insertion mechanism has also been employed Larock R.C., Doty M.J., Han X. Tetrahedron Lett. 39:1998;5143-5146.
13. For recent examples, see: (a) Cacchi S., Fabrizi G., Goggiomani A. Heterocycles. 56:2002;613-632 (b) Panda A.K., Parthasarathy M.R. Indian J. Chem. Sect. B. 2001;628-631 (c) Hu Y., Yang Z. Org. Lett. 3:2001;1387-1390 (d) Frackenpohl J., Braje W.M., Hoffmann H.M.R. J. Chem. Soc., Perkin Trans. 1. 2001;47-65 (e) Hiroya K., Suzuki N., Yasuhara A., Egawa Y., Kasano A., Sakamoto T. J. Chem. Soc., Perkin Trans. 1. 2000;4339-4346. A similar reaction using internal alkynes proceeding through an alkyne insertion mechanism has also been employed Larock R.C., Doty M.J., Han X. Tetrahedron Lett. 39:1998;5143-5146.
14. For recent examples, see: (a) Cacchi S., Fabrizi G., Goggiomani A. Heterocycles. 56:2002;613-632 (b) Panda A.K., Parthasarathy M.R. Indian J. Chem. Sect. B. 2001;628-631 (c) Hu Y., Yang Z. Org. Lett. 3:2001;1387-1390 (d) Frackenpohl J., Braje W.M., Hoffmann H.M.R. J. Chem. Soc., Perkin Trans. 1. 2001;47-65 (e) Hiroya K., Suzuki N., Yasuhara A., Egawa Y., Kasano A., Sakamoto T. J. Chem. Soc., Perkin Trans. 1. 2000;4339-4346. A similar reaction using internal alkynes proceeding through an alkyne insertion mechanism has also been employed Larock R.C., Doty M.J., Han X. Tetrahedron Lett. 39:1998;5143-5146.
15. For recent examples, see: (a) Cacchi S., Fabrizi G., Goggiomani A. Heterocycles. 56:2002;613-632 (b) Panda A.K., Parthasarathy M.R. Indian J. Chem. Sect. B. 2001;628-631 (c) Hu Y., Yang Z. Org. Lett. 3:2001;1387-1390 (d) Frackenpohl J., Braje W.M., Hoffmann H.M.R. J. Chem. Soc., Perkin Trans. 1. 2001;47-65 (e) Hiroya K., Suzuki N., Yasuhara A., Egawa Y., Kasano A., Sakamoto T. J. Chem. Soc., Perkin Trans. 1. 2000;4339-4346. A similar reaction using internal alkynes proceeding through an alkyne insertion mechanism has also been employed Larock R.C., Doty M.J., Han X. Tetrahedron Lett. 39:1998;5143-5146.
16. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
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20. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
21. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
22. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
23. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
24. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
25. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
26. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
27. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
28. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
29. (a) Zhang Y., Herndon J.W. J. Org. Chem. 67:2002;4177-4185 (b) Moser W.H., Sun L., Huffman J.C. Org. Lett. 3:2001;3389-3391 (c) Moreno I., Tellitu I., San Martin R., Dominguez E. Synlett. 2001;1161-1163 (d) Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S. Chem. Pharm. Bull. 49:2001;881-886 (e) Ho J.H., Ho T.I., Liu R.S.H. Org. Lett. 3:2001;409-411 (f) Bandyopadhyay M., Datta K., Mal D. J. Indian Chem. Soc. 76:1999;551-556 (g) Barluenga J., Tomas M., Rubio E., Lopez-Pelegrin J.A., Garcia-Granda S., Perez Priede M. J. Am. Chem. Soc. 121:1999;3065-3071 (h) Maeyama K., Iwasawa N. J. Org. Chem. 64:1999;1344-1346 (i) Sun L., Liebeskind L.S. J. Org. Chem. 60:1995;8194-8203 (j) Chen Y.P., Chantegrel B., Deshayes C. Heterocycles. 41:1995;175-186 (k) Merlic C.A., Roberts W.M. Tetrahedron Lett. 34:1993;7379-7382 (l) Danheiser R.L., Brisbois R.G., Kowalczyk J.J., Miller R.F. J. Am. Chem. Soc. 112:1990;3093-3100 (m) Wulff W.D., McCallum J.S., Kunng F.A. J. Am. Chem. Soc. 110:1988;7419-7434 (n) Yamashita A., Toy A., Scahill T.A. J. Org. Chem. 54:1989;3625-3634.
30. For previous syntheses: (a) Mali R.S., Massey A.P. J. Chem. Res. Synopses. 1998;230-231 (b) Aoyagi Y., Mizusaki T., Hatori A., Asakura T., Aihara T., Inaba S., Hayatsu K., Ohta A. Heterocycles. 41:1995;1077-1084 (c) Schreiber F.G., Stevenson R. J. Chem. Soc., Perkin Trans. 1. 1976;1514-1518 (d) Schreiber F.G., Stevenson R. Chem. Lett. 1975;1257-1258 (e) Ritchie E., Taylor R. Aust. J. Chem. 22:1969;1329-1330.
31. For previous syntheses: (a) Mali R.S., Massey A.P. J. Chem. Res. Synopses. 1998;230-231 (b) Aoyagi Y., Mizusaki T., Hatori A., Asakura T., Aihara T., Inaba S., Hayatsu K., Ohta A. Heterocycles. 41:1995;1077-1084 (c) Schreiber F.G., Stevenson R. J. Chem. Soc., Perkin Trans. 1. 1976;1514-1518 (d) Schreiber F.G., Stevenson R. Chem. Lett. 1975;1257-1258 (e) Ritchie E., Taylor R. Aust. J. Chem. 22:1969;1329-1330.
32. For previous syntheses: (a) Mali R.S., Massey A.P. J. Chem. Res. Synopses. 1998;230-231 (b) Aoyagi Y., Mizusaki T., Hatori A., Asakura T., Aihara T., Inaba S., Hayatsu K., Ohta A. Heterocycles. 41:1995;1077-1084 (c) Schreiber F.G., Stevenson R. J. Chem. Soc., Perkin Trans. 1. 1976;1514-1518 (d) Schreiber F.G., Stevenson R. Chem. Lett. 1975;1257-1258 (e) Ritchie E., Taylor R. Aust. J. Chem. 22:1969;1329-1330.
33. For previous syntheses: (a) Mali R.S., Massey A.P. J. Chem. Res. Synopses. 1998;230-231 (b) Aoyagi Y., Mizusaki T., Hatori A., Asakura T., Aihara T., Inaba S., Hayatsu K., Ohta A. Heterocycles. 41:1995;1077-1084 (c) Schreiber F.G., Stevenson R. J. Chem. Soc., Perkin Trans. 1. 1976;1514-1518 (d) Schreiber F.G., Stevenson R. Chem. Lett. 1975;1257-1258 (e) Ritchie E., Taylor R. Aust. J. Chem. 22:1969;1329-1330.
34. For previous syntheses: (a) Mali R.S., Massey A.P. J. Chem. Res. Synopses. 1998;230-231 (b) Aoyagi Y., Mizusaki T., Hatori A., Asakura T., Aihara T., Inaba S., Hayatsu K., Ohta A. Heterocycles. 41:1995;1077-1084 (c) Schreiber F.G., Stevenson R. J. Chem. Soc., Perkin Trans. 1. 1976;1514-1518 (d) Schreiber F.G., Stevenson R. Chem. Lett. 1975;1257-1258 (e) Ritchie E., Taylor R. Aust. J. Chem. 22:1969;1329-1330.
35. (a) Labaudiniere L., Hanaizi J., Normant J.F. J. Org. Chem. 57:1992;6903-6908 (b) Duboudin J.G., Jousseaume B., Bonakdar A. J. Organomet. Chem. 168:1979;227-232.
36. (a) Labaudiniere L., Hanaizi J., Normant J.F. J. Org. Chem. 57:1992;6903-6908 (b) Duboudin J.G., Jousseaume B., Bonakdar A. J. Organomet. Chem. 168:1979;227-232.
37. Puentes de Diaz A.M. Phytochemistry. 44:1997;345-346.
38. (a) Mendonca P.P., Araujo A.R., Young M.C.M., Giesbrecht A.M. da Silva Bolzani. V., Phytochemistry. 55:2000;597-601 (b) Hasegawa, H.; Sakai, S.; Aimi, N.; Takayama, H.; Koyano, T. Jpn. Kokai Tokkyo Koho; 1996, CODEN: JKXXAF JP 08231396 A2 19960910 Heisei; Chem. Abstr. 1996, 126, 1171.
39. (a) Mendonca P.P., Araujo A.R., Young M.C.M., Giesbrecht A.M. da Silva Bolzani. V., Phytochemistry. 55:2000;597-601 (b) Hasegawa, H.; Sakai, S.; Aimi, N.; Takayama, H.; Koyano, T. Jpn. Kokai Tokkyo Koho; 1996, CODEN: JKXXAF JP 08231396 A2 19960910 Heisei; Chem. Abstr. 1996, 126, 1171.
40. (a) Mendonca P.P., Araujo A.R., Young M.C.M., Giesbrecht A.M. da Silva Bolzani. V., Phytochemistry. 55:2000;597-601 (b) Hasegawa, H.; Sakai, S.; Aimi, N.; Takayama, H.; Koyano, T. Jpn. Kokai Tokkyo Koho; 1996, CODEN: JKXXAF JP 08231396 A2 19960910 Heisei; Chem. Abstr. 1996, 126, 1171.
41. Hirano T., Gotoh M., Oka K. Life Sci. 55:1994;1061-1069.
42. 1c cyclization onto the enyne was favored over Dötz-type processes; selectivity was attributed to the site of chromium complexation.
43. 1c cyclization onto the enyne was favored over Dötz-type processes; selectivity was attributed to the site of chromium complexation.
44. 1c cyclization onto the enyne was favored over Dötz-type processes; selectivity was attributed to the site of chromium complexation.
45. De Meijere A. Pure Appl. Chem. 68:1996;61-72.
46. Stone G.B., Liebeskind L.S. J. Org. Chem. 55:1990;4614-4622.
47. Gem vinylic di-Grignard reagents have been obtained under similar conditions and might account for the formation of 17 Duboudin J.G., Jousseaume B. Synth. Comm. 9:1979;53-56.
48. For a related process, see: Hagiwara H., Coshi T., Fujimoto H., Sugino E., Hibino S. Tetrahedron. 56:2000;5807-5811.
49. The conversion of 26 to 22 can be induced by transition metals. (a) Merlic C.A., Pauly M.E. J. Am. Chem. Soc. 118:1996;11319-11320 (b) Katsuya M., Iwasawa N. J. Org. Chem. 64:1999;1344-1346.
50. The conversion of 26 to 22 can be induced by transition metals. (a) Merlic C.A., Pauly M.E. J. Am. Chem. Soc. 118:1996;11319-11320 (b) Katsuya M., Iwasawa N. J. Org. Chem. 64:1999;1344-1346.
51. Danheiser R.L., Gould A.E., Fernandez de la Pradilla R., Helgason A.L. J. Org. Chem. 59:1994;5514-5515.
52. This compound is chromatographically similar to the major product, alcohol 13 . The mixture of this compound and 13 was subjected to the Sonogashira coupling with trimethylsilylacetylene in anticipation that only 13 would couple and thus the chromatograhic purification of 13 could be avoided. This proved not to be the case.
53. Lee D.G., Brown K.C., Karaman H. Can. J. Chem. 64:1986;1054-1059.
54. Loss of a aryl-bound methyl is a prominent fragmentation pathway in related carboxylic acid analogs of 22 Schaldach B., Grützmacher H.F. Org. Mass Spectrosc. 15:1980;175-181.
55. Sasaki Y., Suzuki M., Hibino T., Karai K. Chem. Pharm. Bull. 15:1967;599-607.