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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.

Publication ,  Journal Article
Lee, K; Kim, H; Hong, J
Published in: Organic letters
November 2009

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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Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

November 2009

Volume

11

Issue

22

Start / End Page

5202 / 5205

Related Subject Headings

  • Temperature
  • Stereoisomerism
  • Pyrans
  • Organic Chemistry
  • Molecular Conformation
  • 34 Chemical sciences
  • 03 Chemical Sciences
 
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

November 2009

Volume

11

Issue

22

Start / End Page

5202 / 5205

Related Subject Headings

  • Temperature
  • Stereoisomerism
  • Pyrans
  • Organic Chemistry
  • Molecular Conformation
  • 34 Chemical sciences
  • 03 Chemical Sciences