Synthetic studies towards pentacyclic quassinoids: Total synthesis of unnatural (-)-14-epi-samaderine e and natural (-)-samaderine y from (S)-(+)-carvone

Tony K.M. Shing, Ying Yeung Yeung

研究成果: Article査読

12 被引用数 (Scopus)

抄録

First total syntheses of unnatural (-)-14-epi-samaderine E (5) and natural (-)-samaderine Y (2) were accomplished from (5)-(+)-carvone (6) in 18 and 21 steps, respectively. The syntheses are short, efficient (with an average yield of 80% plus for each transformation), enantiospecific, and produce nine new chiral centers. The crucial points of the syntheses included a regioselective allylic oxidation on ring C, regio- and stereoselective reduction of ketone, a stereocontrolled epoxidation, an epoxymethano-bridge formation, a chemoselective Grignard reaction, an intramolecular Diels-Alder reaction, an intramolecular aldol addition, and a newly developed manganese(III)-catalyzed allylic oxidation on ring A.

本文言語English
ページ(範囲)8367-8377
ページ数11
ジャーナルChemistry - A European Journal
12
32
DOI
出版ステータスPublished - 2006 11 6

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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