Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: total synthesis of psymberin.

Journal Article (Journal Article)

The total synthesis of psymberin was achieved employing a readily available chiral epoxide to prepare two of the three subunits in the natural product. The key reaction was a highly stereoselective organocatalytic oxa-conjugate addition reaction of α,β-unsaturated ketone catalyzed by primary diamine for the synthesis of the 2,6-trans-tetrahydropyran embedded in psymberin.

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Duke Authors

Hong, Jiyong

Cited Authors

Byeon, SR; Park, H; Kim, H; Hong, J

Published Date

November 2011

Published In

Organic Letters

Volume / Issue

13 / 21

Start / End Page

5816 - 5819

PubMed ID

21988493

Electronic International Standard Serial Number (EISSN)

1523-7052

International Standard Serial Number (ISSN)

1523-7060

Digital Object Identifier (DOI)

10.1021/ol2024289

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