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Org Lett. 2009 Nov 19;11(22):5202-5. doi: 10.1021/ol902125d.

A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A.

Author information

1
Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.

Abstract

The tandem cross-metathesis/thermal S(N)2' reaction was explored for the facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans. The mildness of the thermal conditions allowed for the synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans from base-sensitive substrates without the use of protecting groups. The tandem reaction enabled a protecting-group-free synthesis of (+/-)-diospongin A.

PMID:
19824665
DOI:
10.1021/ol902125d
[Indexed for MEDLINE]

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