Combined Lewis acid catalysts in shotgun process: A convenient synthesis of the female sex pheromone of the red-bollworm moth

Tetrahedron

Volumn 58, Issue 41, 2002, Pages 8211-8217

  Nagano, Yoshifumi ^a   Orita, Akihiro ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Acetylation; Allylation; Lewis acid catalyst; Shotgun process

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; LEWIS ACID; PHEROMONE;

ACETYLATION; ALLYLATION; ARTICLE; CATALYST; DEPROTECTION REACTION; HYBRIDIZATION; MOTH; PRIORITY JOURNAL; SYNTHESIS;

HELICOVERPA ZEA; LEPIDOPTERA;

EID: 0037037935     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00970-5     Document Type: Article

References (32)

1. Orita A., Nagano Y., Nakazawa K., Otera J. Synlett. 2000;599.
2. In this sense, the shotgun process is different from another protocol, parallel recognition, where the multiple reactions proceed simultaneously: (a) Chen J., Otera J. Angew. Chem. Int. Ed. Engl. 37:1998;91. (b) Chen J., Otera J. Tetrahedron Lett. 39:1998;1767. (c) Chen J., Sakamoto K., Orita A., Otera J. Tetrahedron. 54:1998;8411.
3. In this sense, the shotgun process is different from another protocol, parallel recognition, where the multiple reactions proceed simultaneously: (a) Chen J., Otera J. Angew. Chem. Int. Ed. Engl. 37:1998;91. (b) Chen J., Otera J. Tetrahedron Lett. 39:1998;1767. (c) Chen J., Sakamoto K., Orita A., Otera J. Tetrahedron. 54:1998;8411.
4. In this sense, the shotgun process is different from another protocol, parallel recognition, where the multiple reactions proceed simultaneously: (a) Chen J., Otera J. Angew. Chem. Int. Ed. Engl. 37:1998;91. (b) Chen J., Otera J. Tetrahedron Lett. 39:1998;1767. (c) Chen J., Sakamoto K., Orita A., Otera J. Tetrahedron. 54:1998;8411.
5. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
6. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
7. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
8. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
9. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
10. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
11. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
12. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
13. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
14. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
15. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
16. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
17. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
18. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
19. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
20. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
21. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
22. Isolation: (a) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G.J. Insect. Physiol. 21:1975;1091. (b) Henrick C.A. Tetrahedron. 33:1977;1845. Synthesis: (c) Nesbitt B.F., Beevor P.S., Cole R.A., Lester R., Poppi R.G. Tetrahedron Lett. 1973;4669. (d) Mori K. Tetrahedron. 30:1974;3807. (e) Babler J.H., Martin M.J. J. Org. Chem. 42:1977;1799. (f) Babler J.H., Invergo B.J. J. Org. Chem. 44:1979;3723. (g) Mandai T., Yasuda H., Kaito M., Tsuji J., Yamaoka R., Fukami H. Tetrahedron. 35:1979;309. (h) Yasuda A., Tanaka S., Yamamoto H., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;1752. (i) Wollenberg R.H., Peries R. Tetrahedron Lett. 1979;297. (j) Knox G.R., Thom I.G. J. Chem. Soc., Chem. Commun. 1981;373. (k) Rossi R., Carpita A., Quirici M.G. Tetrahedron. 37:1981;2617. (l) Ranganathan S., Kumar R., Maniktala V. Synth. Commun. 12:1982;921. (m) Yamamoto Y., Saito Y., Maruyama K. Tetrahedron Lett. 23:1982;4597. (n) Snider B.B., Phillips G.B. J. Org. Chem. 48:1983;464. (o) Hayashi T., Yanagida M., Matsuda Y., Oishi T. Tetrahedron Lett. 24:1983;2665. (p) Bloch R., Abecassis J., Hassan D. Can. J. Chem. 62:1984;2019. (q) Hsio C.-N., Shechter H. Tetrahedron Lett. 25:1984;1219 (r) Sato T., Okura S., Otera J., Nozaki H. Tetrahedron Lett. 28:1987;6299.
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27. 2: Masaki Y., Imada T., Kawai M. Chem. Pharm. Bull. 42:1994;179.
28. 2: Masaki Y., Imada T., Kawai M. Chem. Pharm. Bull. 42:1994;179.
29. 2: Masaki Y., Imada T., Kawai M. Chem. Pharm. Bull. 42:1994;179.
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31. Orita A., Sakamoto K., Hamada Y., Mitsutome A., Otera J. Tetrahedron. 55:1999;2899.
32. 2 can quench the reaction instantaneously to allow the quantitative analysis.