Pseudo-C3-Symmetric Tertiary Alcohol Building Block via Group-Selective Hydroalumination: A Synthesis of (-)-Malyngolide

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1741-1744

  Suzuki, Takao ^a   Ohmori, Ken ^a   Suzuki, Keisuke ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALUMINUM; ANTIINFECTIVE AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MALYNGOLIDE; PYRONE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALCOHOLS; ALUMINUM; ANTI-BACTERIAL AGENTS; INDICATORS AND REAGENTS; PYRONES;

EID: 0035979046     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015943v     Document Type: Article

References (16)

1. For isolation of 1, see: Cardllina, J. H.; Moore, R. E.; Arnold, E. V.; Clardy, J. J. Org. Chem. 1979, 44, 4039. For previous total syntheses, see: (a) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
2. For isolation of 1, see: Cardllina, J. H.; Moore, R. E.; Arnold, E. V.; Clardy, J. J. Org. Chem. 1979, 44, 4039. For previous total syntheses, see: (a) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
3. (b) Trost, B. M.; Tang, W.; Schulte, J. L. Org. Lett. 2000, 2, 4013. Reference 1a reports the most recent synthesis and ref 1b the next most recent, compiling the 27 previous syntheses.
4. Ohmori, K.; Suzuki, T.; Taya, K.; Tanabe, D.; Ohta, T.; Suzuki, K. Org. Lett. 2001, 3, 1057.
5. This marine natural product, which is a kind of symbolic compound for synthetic practice, and as many as 29 chiral synthetic routes have been documented with the present synthesis being the 30th one!
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7. 2, hexane/EtOAc = 95/5) gave 5 (302 mg, 91%, >99% ds) as a colorless oil.
8. 2O for the hydroalumination of 7 only gave a 6/4 group selectivity of 5 and epi-5, which were separated and used for the structure assignment. Thus, epi-5 was similarly converted to the cyclic derivative epi-9, which showed again diagnostic NOE as shown in Figure 2.
9. 2, hexane/EtOAc = 85/15) gave 4 (160 mg, 79%, >99% ds) as a colorless oil.
10. 3).
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