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.

Journal Article (Journal Article)

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.

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Duke Authors

Hong, Jiyong

Cited Authors

Lee, K; Kim, H; Hong, J

Published Date

November 2009

Published In

Organic Letters

Volume / Issue

11 / 22

Start / End Page

5202 - 5205

PubMed ID

19824665

Electronic International Standard Serial Number (EISSN)

1523-7052

International Standard Serial Number (ISSN)

1523-7060

Digital Object Identifier (DOI)

10.1021/ol902125d

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