Asymmetric synthesis of umuravumbolide1

Organic Letters

Volumn 3, Issue 1, 2001, Pages 19-20

  Venkat Ram Reddy, M ^a   Rearick, John P ^a   Hoch, Nyssa ^a   Veeraraghavan Ramachandran, P ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DESACETYLUMURAVUMBOLIDE; PYRONE DERIVATIVE; UMURAVUMBOLIDE;

ANGIOSPERM; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; LAMIACEAE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANTS, MEDICINAL; PYRONES; STEREOISOMERISM;

EID: 0035843312     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006583z     Document Type: Article

References (17)

1. Contribution 8 from the Herbert C. Brown Center for Borane Research.
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8. Ketone 2 was prepared via Jones oxidation of commercially available 1-heptyn-3-ol.
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10. (b) Alpine-Borane is the registered trademark of Aldrich Chemical Co.
11. 3.
12. To confirm the efficacy of this upgradation procedure, we prepared 1-butyn-3-ol and 1-octyn-3-ol of 72% and 76% ee, respectively, by Alpine-Borane (84% ee) reduction of the corresponding ketone and upgraded them to 99% ee via the 3,5-dintrobenzoate.
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14. 1H NMR spectroscopy. The configuration is based on analogy for allylborations with 7. This was confirmed by the rotation of the target molecule.
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16. The observed selectivity for the ring-closing metathesis reaction has precedence. Wright, D. L. Curr. Org. Chem. 1999, 3, 211.
17. Myers, A. G.; Gin, D. Y.; Rogers, D. H. J. Am. Chem. Soc. 1994, 116, 4697.