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Stereoselective synthesis of β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones.

Abstract:
Zinc or a chromium(II) source with 3-(bromomethyl)furan-2(5H)-one (3) and an aldehyde gives β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones 5 in good yields and high diastereoselectivities. The methodology is demonstrated in concise syntheses of (±)-hydroxymatairesinol (8) and (±)-methylenolactocin (10) by subsequent arylboronate conjugate addition and translactonization, respectively.
Publication status:
Published

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Publisher copy:
10.1021/ol200711f

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic letters
Volume:
13
Issue:
10
Pages:
2594-2597
Publication date:
2011-05-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:b687be1e-1b4d-4e09-a39a-79cbfc6449b9
Source identifiers:
131232
Local pid:
pubs:131232

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