Diastereoselective total synthesis of both enantiomers of epolactaene

Yujiro Hayashi, Jun Kanayama, Junichiro Yamaguchi, Mitsuru Shoji

研究成果: Article査読

41 被引用数 (Scopus)

抄録

A stereocontrolled total synthesis of both the (+)- and (-)-epolactaene ((+)- and (-)-1) enantiomers from tetrahydropyran-2-ol is described. The following reactions in this synthesis are particularly noteworthy: (1) the stereoselective construction of the conjugated (E,E,E)-triene by a combination of kinetic deprotonation and thermodynamic equilibration, (2) the E-selective Knoevenagel condensation of β-ketonitrile 33 with a chiral 2-alkoxyaldehyde, (3) a diastereoselective epoxidation achieved using a bulky nucleophile (TrOOLi) and an appropriate protecting group, (4) the mild hydrolysis of an α-epoxy nitrile by silica gel on TLC facilitated by hydroxyl-mediated, intramolecular assistance.

本文言語English
ページ(範囲)9443-9448
ページ数6
ジャーナルJournal of Organic Chemistry
67
26
DOI
出版ステータスPublished - 2002 12月 27

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「Diastereoselective total synthesis of both enantiomers of epolactaene」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル