The Total Synthesis of (±)-Merrilactone A

The Total Synthesis of (±)-Merrilactone A

The total synthesis of the title compound has been accomplished in 20 steps. The key step is a free radical cyclization of vinyl bromide 29 to afford 30. The synthesis also features an efficient Diels−Alder reaction of 2,3-dimethylmaleic anhydride with 1-(tert-butyldimethylsiloxy)-butadiene. The oxe...

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Veröffentlicht in:Journal of the American Chemical Society 2002-03, Vol.124 (10), p.2080-2081
Hauptverfasser: Birman, Vladimir B, Danishefsky, Samuel J
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Illicium - chemistry
Lactones - chemical synthesis
Organic chemistry
Preparations and properties
Sesquiterpenes - chemical synthesis
Stereoisomerism
Terpenoids
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Beschreibung
Zusammenfassung:The total synthesis of the title compound has been accomplished in 20 steps. The key step is a free radical cyclization of vinyl bromide 29 to afford 30. The synthesis also features an efficient Diels−Alder reaction of 2,3-dimethylmaleic anhydride with 1-(tert-butyldimethylsiloxy)-butadiene. The oxetane moiety of merrilactone A is fashioned via a Payne-like rearrangement of a hydroxyepoxide (see 2 → 1).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja012495d