Stereoselective total synthesis of lysocellin, the representative polyether antibiotic of the lysocellin family. Part 2. Synthesis of C10-C23 subunit via construction of two rings (B and C) and its condensation with C1-C9 subunit to achieve the total synthesis of lysocellin

Tetrahedron

Volumn 52, Issue 2, 1996, Pages 551-564

  Horita, Kiyoshi ^a   Tanaka, Kazuhiro ^a   Inoue, Takayuki ^a   Yonemitsu, Osamu ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LYSOCELLIN; POLYETHER ANTIBIOTIC AGENT;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030033471     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00906-X     Document Type: Article

References (20)

1. Chiral synthesis of polyketide derived natural products, 52. For part 51, see: K. Horita, T. Inoue, K. Tanaka, and O. Yonemistu, Tetrahedron, in press (the preceding paper).
2. a) I. Noda, K. Horita, Y. Oikawa, and O. Yonemitsu, Tetrahedron Lett., 31, 6035 (1990);
3. b) K. Horita, I. Noda, K. Tanaka, Y. Oikawa, and O. Yonemitsu, Tetrahedron, 49, 5997 (1993).
4. K. Horita, K. Tanaka, and O. Yonemitsu, Chem. Pharm. Bull., 41, 2044 (1993).
5. Unless otherwise noted, numbering is based on that of lysocellin (1).
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13. a) M. Koenuma and N. Otake, J. Antibiot., 30, 819 (1977);
14. b) D. A. Evans, R. P. Polmaszek, K. M. DeVries, D. E. Guinn, and D. J. Mathre, J. Am. Chem. Soc., 113, 7613 (1991).
15. a) E. Ebata, H. Kasahara, K. Sekine, and Y. Inoue, J. Antibiot., 28, 118 (1975);
16. b) N. Otake, M. Koemura, H. Kinase, S. Sato, and Y. Saito, J. Chem. Soc., Chem. Commun., 92 (1975);
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18. 3N gave a C17,18-anhydro compound with loss of MeOH in quantitative yield.
19. In THF or in ether at 0°C, concomitant loss of the TMS group was observed.
20. Three products (3mg, 22%) other than 1 sodium salt were isolated by silical gel thin-layer chromatography and each Mass fragmentation pattern was almost identical to that of 1 sodium salt.