Partially hydroxylated 2,5-disubstituted bis-tetrahydrofurans from carbohydrates

Chemistry - A European Journal

Volumn 6, Issue 8, 2000, Pages 1337-1345

  Bruns, Rainer ^a   Kopf, Jürgen ^b   Köll, Peter ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Annonaceous acetogenins; Carbohydrates; Cyclizations; Natural products; Synthetic methods; Tetrahydrofurans

Indexed keywords

ACETOGENIN; CARBOHYDRATE; GLUCOSE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; EPOXIDATION; HYDROXYLATION; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034646764     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000417)6:8<1337::aid-chem1337>3.0.co;2-k     Document Type: Article

References (60)

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12. Reviews on synthesis, see: a) R. Hoppe, H.-D. Scharf, Synthesis 1995, 1447-1464 b) B. Figadère, Acc. Chem. Res. 1995, 28, 359-365 c) U. Koert, Synthesis 1995, 115-132 d) B. Figadère, A. Cavé, in Studies in Natural Products Chemistry, Vol. 18 (Eds.: A.-ur Rahmann), Elsevier Science, 1996, pp. 193-227 e) J. A. Marshall, K. W. Hinkle, C. E. Hagedron, Isr. J. Chem. 1997, 37, 97-107.
13. Reviews on synthesis, see: a) R. Hoppe, H.-D. Scharf, Synthesis 1995, 1447-1464 b) B. Figadère, Acc. Chem. Res. 1995, 28, 359-365 c) U. Koert, Synthesis 1995, 115-132 d) B. Figadère, A. Cavé, in Studies in Natural Products Chemistry, Vol. 18 (Eds.: A.-ur Rahmann), Elsevier Science, 1996, pp. 193-227 e) J. A. Marshall, K. W. Hinkle, C. E. Hagedron, Isr. J. Chem. 1997, 37, 97-107.
14. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
15. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
16. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
17. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, J. Jiang, H. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
18. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
19. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
20. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
21. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
22. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
23. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
24. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
25. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
26. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
27. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
28. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
29. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
30. Recent total synthesis of annonaceous acetogenins: a) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057 b) J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306 c) H. Makabe, A. Tanaka, T. Oritani, Tetrahedron 1998, 54, 6329-6340 d) S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018 e) A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868 f) J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071 g) S. E. Schaus, J. Branalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 4876-4877 h) P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284 i) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726 j) S. Takashashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730 k) J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975 I) S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344; Angew. Chem. Int. Ed. 1999, 38, 1263-1266 m) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron: Asymmetry 1999, 10, 667-670 n) Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980 o) Q. Yu, Z.-J. Yao, X.-G. Chen, Y.-L. Wu, J. Org. Chem. 1999, 64, 2440-2445 p) Q. Yu, Y. Wu, H. Ding, Y.-L. Wu, J. Chem. Soc. Perkin Trans. 1 1999, 1183-1188.
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58. [17] name: 2,5:6,9-dianhydro-7,8,11-tri-O-benzyl-3,4,10-trideoxy-D-threo-D-galacto- undecitol.
59. [17] name: 1,7,8,11-tetra-O-acetyl-2:5;6:9-dianhydro-3,4,10-trideoxy-D-threo-D-galacto- undecitol.
60. [17] name: 2,5:6,9-dianhydro-3,4,10-trideoxy-D-threo-D-galacto-undecitol.