Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 7, Pages 2602-2611Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0626459
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Funding
- NCRR NIH HHS [S10 RR017915-01A1, S10 RR017915] Funding Source: Medline
- NIGMS NIH HHS [R01 GM065338-03, R01 GM065338, GM-65388, R01 GM065338-01, R01 GM065388, R01 GM065338-02, R01 GM065338-04] Funding Source: Medline
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A reductive cyclization strategy was applied to the synthesis of attenol A. This nontraditional approach to the spiroacetal structure illustrated several advantages of the reductive cyclization methodology. The attenol A core was formed in a carbon-carbon bond coupling that gave rise to a previously inaccessible spiroacetal epimer, a new method to synthesize thioketene acetals from a phenyl sulfone was realized, and the configurational stability of a nonanomeric spiroacetal was evaluated. A minor byproduct in the reductive cyclization reaction was identified that for the first time allowed direct evaluation of the stereoselectivity in a reductive cyclization of a dialkyloxy alkyllithium reagent.
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