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Total synthesis of (+)-cis-sylvaticin: double oxidative cyclization reactions catalyzed by osmium.

Abstract:
The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm its structure. The natural product was then prepared by a short sequence of reactions that is exceptionally concise: the final route being just 13 linear steps and 19 chemical operations in total.
Publication status:
Published

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Publisher copy:
10.1021/ja0660148

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Harris, RM More by this author
Burrows, J More by this author
Journal:
Journal of the American Chemical Society
Volume:
128
Issue:
42
Pages:
13704-13705
Publication date:
2006-10-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:9429707c-384b-41a0-867f-c11808260b4b
Source identifiers:
33636
Local pid:
pubs:33636

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