Total synthesis of reveromycin A

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2153-2156

  Shimizu, Takeshi ^a   Masuda, Tsutomu ^a   Hiramoto, Katsuya ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PYRAN DERIVATIVE; REVEROMYCIN A; SPIRO COMPOUND;

ARTICLE; CHEMISTRY; CONFORMATION; STREPTOMYCES; SYNTHESIS;

ANTIBIOTICS, ANTINEOPLASTIC; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; PYRANS; SPIRO COMPOUNDS; STREPTOMYCES;

EID: 0034644036     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0060634     Document Type: Article

References (22)

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12. 9
13. The synthetic schemes of 9 and 10 are included in Supporting Information.
14. The computational calculations were performed using MM2*/ MacroModel 6.0.
15. 3, 2,6-lutidine) induced transacetalization to give the corresponding 5,6-spiroketal.
16. Deprotection of the TBDPS group in 17 or 20 with TBAF in THF at room temperature afforded the C20-succinate via the migration.
17. Corey, E. J.; Katzenellenbogen, J. A.; Roman, S. A.; Gilman N. W. Tetrahedron Lett. 1971, 21, 1821-1824.
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19. 5 resulted in the recovery of 23. This result would be due to the steric hindrance of the C19 dienoic ester.
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22. Treatment of 27 with HF·Py in THF or TBAF in DMF resulted in the recovery or decomposition, respectively.