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A cycloaddition-rearrangement approach to the squalestatins

Abstract:
Reaction of diazodiketoester 4 with methyl glyoxylate in toluene in the presence of catalytic rhodium(II) acetate generates the 6,8- dioxabicyclo[3.2.1]octane 5 as a single regio- and stereo-isomer in good yield. Elaboration provides a suitable alcohol 7 for acid-catalysed rearrangement to give the 2,8-dioxabicyclo-[3.2.1]octane skeleton 8 of the squalestatins.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON LETTERS
Volume:
37
Issue:
26
Pages:
4623-4626
Publication date:
1996-06-24
DOI:
ISSN:
0040-4039
URN:
uuid:7dbc3da3-90d4-4ef4-b1ca-af53e3e9faba
Source identifiers:
45244
Local pid:
pubs:45244

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