Synthesis of (4R,12S,15S,16S,19R,20R,34S)-muricatetrocin and (4R,12R,15S,16S,19R,20R,34S)-muricatetrocin, two potent inhibitors of mitochondrial complex I

European Journal of Organic Chemistry

Volumn , Issue 12, 2000, Pages 2207-2217

  Bäurle, Stefan ^a   Peters, Ulf ^a   Friedrich, Thorsten ^b   Koert, Ulrich ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

^b HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Complex I inhibitors; Howiicin E; Muricatetrocin; Natural products; Synthetic methods; Total synthesis

Indexed keywords

ENZYME INHIBITOR; HOWIICIN E; MURICATETROCIN; MURICATETROCIN A; MURICATETROCIN B; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); ROTENONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATTLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HEART MITOCHONDRION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0033934490     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200006)2000:12<2207::AID-EJOC2207>3.0.CO;2-C     Document Type: Article

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18. Nonadjacent THF-THP: [4a] S. Takahashi, T. Nakata, Tetrahedron Lett. 1999, 40, 723-726. [4b] S. Takahashi, T. Nakata, Tetrahedron Lett. 1999, 40, 727-730. [4c] S. Bäurle, S. Hoppen, U. Koert, Angew. Chem. 1999, 111, 1341-1344. - Angew. Chem. Int. Ed. 1999, 38, 1263-1266 . [4d] P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 11279-11284.
19. Tris-THF: [5a] S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015. [5b] S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018.
20. Tris-THF: [5a] S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1997, 119, 12014-12015. [5b] S. C. Sinha, A. Sinha, S. C. Sinha, E. Keinan, J. Am. Chem. Soc. 1998, 120, 4017-4018.
21. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
22. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
23. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
24. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
25. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
26. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
27. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
28. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
29. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
30. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
31. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
32. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
33. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
34. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
35. Adjacent bis-THF: [6a] J. A. Marshall, H. Jiang, J. Nat. Prod. 1999, 62, 1123-1127. [6b] S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 7067-7073. [6c] A. Sinha, S. C. Sinha, S. C. Sinha, E. Keinan, J. Org. Chem. 1999, 64, 2381-2386. [6d] J. A. Marshall, H. Jiang, J. Org. Chem. 1999, 64, 971-975. [6e] U. Emde, U. Koert, Tetrahedron Lett. 1999, 40, 5979-5982. [6f] Z.-M. Wang, S.-K. Tian, M. Shi, Tetrahedron Lett. 1999, 40, 977-980. [6g] J. A. Marshall, K. W. Hinkle, Tetrahedron Lett. 1998, 39, 1303-1306. [6h] A. Yazbak, S. C. Sinha, E. Keinan, J. Org. Chem. 1998, 63, 5863-5868. [6i] B. M. Trost, T. L. Calkins, C. G. Bochet, Angew. Chem. 1997, 109, 2746-2748. - Angew. Chem. Int. Ed. Engl. 1997, 36, 2632-2634. [6i] J. A. Marshall, K. W. Hinkle, J. Org. Chem. 1997, 62, 5989-5995. [6k] J. A. Marshall, M. Chen, J. Org. Chem. 1997, 62, 5996-6000. [6l] T. R. Hoye, L. Tan, J. Am. Chem. Soc. 1996, 118, 1801-1802. [6m] S. C. Sinha, A. Sinha, A. Yazbak, E. Keinan, J. Org. Chem. 1996, 61, 7640-7641. [6n] I. Wöhrle, A. Claßen, M. Peterek, H.-D. Scharf, Tetrahedron Lett. 1996, 37, 7001-7004. For work prior to 1996 see ref. 1.
36. Nonadjacent bis-THF: [7a] J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071. [7b] H. Makabe, A. Tanaka, T. Oritani, Tetrahedron Lett. 1997, 38, 4247-4250.
37. Nonadjacent bis-THF: [7a] J. A. Marshall, H. Jiang, J. Org. Chem. 1998, 63, 7066-7071. [7b] H. Makabe, A. Tanaka, T. Oritani, Tetrahedron Lett. 1997, 38, 4247-4250.
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