Artificial Anthraquinone - Carbohydrate Hybrids: Design, Synthesis, DNA Binding, and Cytotoxicity

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 24, 1997, Pages 2748-2750

  Toshima, Kazunobu ^a   Ouchi, Hiromi ^a   Okazaki, Yoriko ^a   Kano, Takaaki ^a   Moriguchi, Makoto ^a   Asai, Akira ^b   Matsumura, Shuichi ^a  

^a KEIO UNIVERSITY   (Japan)

^b KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

Asymmetric synthesis; Butenolides; Dihydroxylations; Furanones; Lactones

Indexed keywords

EID: 0032491821     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199727481     Document Type: Article

References (62)

1. Recent reviews: a) H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; b) G. Poli, C. Scolastico, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e, pp. 4547-4598.
2. Recent reviews: a) H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; b) G. Poli, C. Scolastico, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952-, Vol. E21e, pp. 4547-4598.
3. Recent syntheses of nonracemic γ-chiral butenolides: a) B. Figadère, J.-F. Peyrat, A. Cavé, J. Org. Chem. 1997, 62, 3428-3429; b) J. A. Marshall, M. A. Wolf, E. M. Wallace, ibid. 1997, 62, 367-371; c) A. van Oeveren, B. L. Feringa, ibid. 1996, 61, 2920-2921.
4. Recent syntheses of nonracemic γ-chiral butenolides: a) B. Figadère, J.-F. Peyrat, A. Cavé, J. Org. Chem. 1997, 62, 3428-3429; b) J. A. Marshall, M. A. Wolf, E. M. Wallace, ibid. 1997, 62, 367-371; c) A. van Oeveren, B. L. Feringa, ibid. 1996, 61, 2920-2921.
5. Recent syntheses of nonracemic γ-chiral butenolides: a) B. Figadère, J.-F. Peyrat, A. Cavé, J. Org. Chem. 1997, 62, 3428-3429; b) J. A. Marshall, M. A. Wolf, E. M. Wallace, ibid. 1997, 62, 367-371; c) A. van Oeveren, B. L. Feringa, ibid. 1996, 61, 2920-2921.
6. Recent syntheses of nonracemic γ-chiral γ-lactones: a) W.-Y. Yu, C. Bensimon, H. Alper, Chem. Eur. J. 1997, 3, 417-423; b) T. Chevtchouk, J. Ollivier, J. Salaün, Tetrahedron: Asymmetry 1997, 8, 1011-1014; c) A.-M. Fernandez, J.-C. Plaquevent, L. Duhamel, J. Org. Chem. 1997, 62, 4007-4014; d) S.-i. Fukuzawa, K. Seki, M. Tatsuzawa, K. Mutoh, J. Am. Chem. Soc. 1997, 119, 1482-1483.
7. Recent syntheses of nonracemic γ-chiral γ-lactones: a) W.-Y. Yu, C. Bensimon, H. Alper, Chem. Eur. J. 1997, 3, 417-423; b) T. Chevtchouk, J. Ollivier, J. Salaün, Tetrahedron: Asymmetry 1997, 8, 1011-1014; c) A.-M. Fernandez, J.-C. Plaquevent, L. Duhamel, J. Org. Chem. 1997, 62, 4007-4014; d) S.-i. Fukuzawa, K. Seki, M. Tatsuzawa, K. Mutoh, J. Am. Chem. Soc. 1997, 119, 1482-1483.
8. Recent syntheses of nonracemic γ-chiral γ-lactones: a) W.-Y. Yu, C. Bensimon, H. Alper, Chem. Eur. J. 1997, 3, 417-423; b) T. Chevtchouk, J. Ollivier, J. Salaün, Tetrahedron: Asymmetry 1997, 8, 1011-1014; c) A.-M. Fernandez, J.-C. Plaquevent, L. Duhamel, J. Org. Chem. 1997, 62, 4007-4014; d) S.-i. Fukuzawa, K. Seki, M. Tatsuzawa, K. Mutoh, J. Am. Chem. Soc. 1997, 119, 1482-1483.
9. Recent syntheses of nonracemic γ-chiral γ-lactones: a) W.-Y. Yu, C. Bensimon, H. Alper, Chem. Eur. J. 1997, 3, 417-423; b) T. Chevtchouk, J. Ollivier, J. Salaün, Tetrahedron: Asymmetry 1997, 8, 1011-1014; c) A.-M. Fernandez, J.-C. Plaquevent, L. Duhamel, J. Org. Chem. 1997, 62, 4007-4014; d) S.-i. Fukuzawa, K. Seki, M. Tatsuzawa, K. Mutoh, J. Am. Chem. Soc. 1997, 119, 1482-1483.
10. Z.-M. Wang, X.-L. Zhang, K. B. Sharpless, S. C. Sinha, A. Sinha-Bagchi, E. Keinan, Tetrahedron Lett. 1992, 33, 6407-6410 describe three examples each for the 4→3 and 4→ent-3 conversion (R = Et, Hex, Ph; ee 92% to >99%).
11. 3 with 86% ee.
12. C. S. Pak, E. Lee, G. H. Lee. J. Org. Chem. 1993, 58, 1523-1530.
13. 3), IR spectra (KBr), and combustion analyses.
14. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem 1978, 43, 2923-2925.
15. Typical procedure for obtaining type-3 γ-lactones from deconjugated esters 4: [18].
16. T values of AD-based product (or the derived butenolide) and of its enantiomer (as observed in the corresponding racemic mixture): 10 50.5 min (110°C; enantiomer 51.4 min); 15 53.6 min (130°C; enantiomer 54.8 min); 23 45.4 min (110°C; enantiomer 44.3 min).
17. Stereostructure: R. Hill, R. van Heyningen, Biochem. J. 1951, 49, 332-335.
18. 2Si-11; from L-glutamic acid in five steps).
19. 2Si-11; from L-glutamic acid in five steps).
20. 2Si-11; from L-glutamic acid in five steps).
21. 2Si-11; from L-glutamic acid in five steps).
22. 2Si-11; from L-glutamic acid in five steps).
23. 2Si-11; from L-glutamic acid in five steps).
24. 2Si-11; from L-glutamic acid in five steps).
25. 2Si-11; from L-glutamic acid in five steps).
26. 2Si-11; from L-glutamic acid in five steps).
27. Stereostructure: J. W. Wheeler, G. M. Happ, J. Araujo, J. M. Pasteels, Tetrahedron Lett. 1972, 4635-4638.
28. Prepared in one step by the general procedure of N. Ragoussis, Tetrahedron Lett. 1987, 28, 93-96.
29. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
30. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
31. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
32. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
33. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
34. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
35. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
36. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
37. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
38. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
39. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
40. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
41. Selected syntheses of (+)-dodecanolide: a) G. Tuynenburg Muys, B. van der Ven, A. P. de Jonge, Nature 1962, 194, 995-996; T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512 (from commercially not available ethyl 4-oxododecanoate in two steps); b) Y. Naoshima, H. Hasegawa, T. Saeki, Agric. Biol. Chem. 1987, 51, 3417-3419 (from diethyl-3-oxoglutarate in four steps).; c) J. P. Vigneron, V. Bloy, Tetrahedron Lett. 1980, 21, 1735-1738 (from 1-undecyn-3-one in four steps); d) H. Kakeya, N. Sakai, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 1877-1881 (from 2-hydroxydecanenitril in six steps); e) C. Bonini, C. Federici, L. Rossi, G. Righi, J. Org. Chem. 1995, 60, 4803-4812 (from octanal in six steps); f) G. C. Paddon-Jones, C. J. Moore, D. J. Brecknell, W. A. König, W. Kitching, Tetrahedron Lett. 1997, 38, 3479-3482 (from L-glutamic acid in six steps); g) T. Ebata, H. Kawakami, K. Koseki, H. Matsushita, Agric. Biol. Chem. 1991, 55, 1685-1686 in continuation of steps described by M. P. Balfe, M. Irwin, J. Kenyon, J. Chem. Soc. 1941, 313-316 (from tetrahydrofurfurol in seven steps); h) V. Cere, C. Mazzini, C. Paolucci, S. Pollicino, A. Fava, J. Org. Chem. 1993, 58, 4567-4571 (from 1,4:3,6-dianhydro-D-mannitol in seven steps); i) T. Sugai, K. Mori, Agric. Biol. Chem. 1984, 48, 2497-2500 [from N-(chloroacetamidoyl)decanoic acid in eight steps]; j) S. Chattopadhyay, V. R. Mamdapur, M. S. Chadha, Tetrahedron 1990, 46, 3667-3672 (from 1,2:5,6-di-O-isopropylidene-D-mannitol in nine steps); k) H. Nemoto, H. Ishibashi, M. Mori, S. Fujita, K. Fukumoto, J. Chem. Soc. Perkin Trans. I 1990, 2835-2840 (from methyl 1-hydroxycyclopropanecarboxylate in ten steps).
42. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
43. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
44. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
45. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
46. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
47. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
48. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
49. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
50. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
51. Selected syntheses of (-)-trans quercus lactone: a) D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67-69; Angew. Chem. Int. Ed. Engl. 1989, 28, 69-71 (from crotyl alcohol in four steps); b) M. Beckmann, H. Hildebrandt, E. Winterfeldt, Tetrahedron Asymmetry 1990, 1, 335-345 in continuation of steps described by K. Matcheva, M. Beckmann, D. Schomburg, H. Winterfeldt, Synthesis 1989, 814-817 (from maleic anhydride and an enantiopure diene in five steps); c) J. P. Marino, R. F. de la Pradilla, Tetrahedron Lett. 1985, 26, 5381-5384 (from trans-1-bromopropene in six steps); d) R. Bloch, L. Gilbert, J. Org. Chem. 1987, 52, 4603-4605 in continuation of steps described by R. Bloch, E. Guibé-Jampel, C. Girard, Tetrahedron Lett. 1985, 26, 4087-4090 (from the Diels-Alder adduct of maleic anhydride and furane in seven steps); e) R. M. Ortuno, R. Merce, J. Font, Tetrahedron 1987, 43, 4497-4506 (from D-ribonolactone in seven steps); f) C. Günter, A. Mosandl, Liebigs Ann. Chem. 1986, 2112-2122 (from pentanal in eight steps); g) D. F. Taber, J. B. Houze, J. Org. Chem. 1994, 59, 4004-4006 (from geraniol in eleven steps). For another multistep synthesis see ref. [3b].
52. Stereostructure: M. Masuda, K. Nishimura, Phytochem. 1971, 10, 1401-1402; M. Masuda, K. Nishimura, Chem. Lett. 1981, 1333-1336.
53. Stereostructure: M. Masuda, K. Nishimura, Phytochem. 1971, 10, 1401-1402; M. Masuda, K. Nishimura, Chem. Lett. 1981, 1333-1336.
54. ADs of disubstituted olefins trans-MeCH=CHR were reported to show 72% ee in the case of 2-butene ("unpublished results" in ref. [1a]), 73% ee in the case of 1-phenylpent-3-en-1-yne (K.-S. Jeong, P. Sjö, K. B. Sharpless, Tetrahedron Lett. 1992, 33, 3833-3836), and 95% ee in the cases of 1-chloro-2-butene (K. P. M. Vanhessche, Z.-M. Wang, K. B. Sharpless, ibid. 1994, 35, 3469-3472) or 4,4-dimethyl-2-pentene ("unpublished results" in ref. [1a]).
55. ADs of disubstituted olefins trans-MeCH=CHR were reported to show 72% ee in the case of 2-butene ("unpublished results" in ref. [1a]), 73% ee in the case of 1-phenylpent-3-en-1-yne (K.-S. Jeong, P. Sjö, K. B. Sharpless, Tetrahedron Lett. 1992, 33, 3833-3836), and 95% ee in the cases of 1-chloro-2-butene (K. P. M. Vanhessche, Z.-M. Wang, K. B. Sharpless, ibid. 1994, 35, 3469-3472) or 4,4-dimethyl-2-pentene ("unpublished results" in ref. [1a]).
56. Method: H.-M. Shieh, G. D. Prestwich, J. Org. Chem. 1981, 46, 4319-4321. Methylations of hydroxylactones analogous to 23 were possible in the absence of HMPA according to A. R. Chamberlin, M. Dezube, S. H. Reich, D. J. Sall, J. Am. Chem. Soc. 1989, 111, 6247-6256.
57. Method: H.-M. Shieh, G. D. Prestwich, J. Org. Chem. 1981, 46, 4319-4321. Methylations of hydroxylactones analogous to 23 were possible in the absence of HMPA according to A. R. Chamberlin, M. Dezube, S. H. Reich, D. J. Sall, J. Am. Chem. Soc. 1989, 111, 6247-6256.
58. a) D. Seebach, Chimia 1985, 39, 147-148;
59. b) D. Seebach, A. K. Beck, A. Studer in Modem Synthetic Methods 1995 (Eds.: B. Ernst, C. Leumann), VCH, Weinheim, 1995, pp. 1-178.
60. The enantiomer of epi-blastmycinone 25 was synthesized by J. Mulzer, T. Schulze, A. Strecker, W. Denzer, J. Org. Chem. 1988, 53, 4098-4103 and M. P. Sibi, J. Lu, C. L. Talbacka, ibid. 1996, 61, 7848-7855, while racemic 25 was synthesized by C. Mukai, O. Kataoka, M. Hanaoka, ibid. 1993, 58, 2946-2952.
61. The enantiomer of epi-blastmycinone 25 was synthesized by J. Mulzer, T. Schulze, A. Strecker, W. Denzer, J. Org. Chem. 1988, 53, 4098-4103 and M. P. Sibi, J. Lu, C. L. Talbacka, ibid. 1996, 61, 7848-7855, while racemic 25 was synthesized by C. Mukai, O. Kataoka, M. Hanaoka, ibid. 1993, 58, 2946-2952.
62. The enantiomer of epi-blastmycinone 25 was synthesized by J. Mulzer, T. Schulze, A. Strecker, W. Denzer, J. Org. Chem. 1988, 53, 4098-4103 and M. P. Sibi, J. Lu, C. L. Talbacka, ibid. 1996, 61, 7848-7855, while racemic 25 was synthesized by C. Mukai, O. Kataoka, M. Hanaoka, ibid. 1993, 58, 2946-2952.