Total synthesis of (±)-symbioimine

Organic Letters

Volumn 8, Issue 24, 2006, Pages 5605-5608

  Zou, Yefen ^a   Che, Qinglin ^a   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; OXYGEN; PHOSPHORANE DERIVATIVE; SULFATE; SYMBIOIMINE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

HETEROCYCLIC COMPOUNDS, 3-RING; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; OXYGEN; PHOSPHORANES; STEREOISOMERISM; SULFATES;

EID: 33846027848     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062333s     Document Type: Article

References (16)

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10. Our original procedure required two steps to hydrolyze a dioxolane protecting group by first converting it to a dimethyl acetal. The sequence has been shortened one step by alkylating ethyl acetoacetate with 3-bromo-1,1-dimethoxypropane rather than 2-(2-bromoethyl)-1,3-dioxolane so that the acetal exchange is not necessary. Full details are provided in the Supporting Information.
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13. 8
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16. 8 Treatment of the phosphonium salt with n-BuLi afforded 11b. Full details are provided in the Supporting Information.