Tremorgenic Indole Alkaloids. 9. Asymmetric Construction of an Advanced F-G-H-Ring Lactone Precursor for the Synthesis of Penitrem D

Amos B. Smith, Ernest G. Nolen, Ryuichi Shirai, Frances R. Blase, Mitsuaki Ohta, Noritaka Chida, Richard A. Hartz, Duke M. Fitch, William M. Clark, Paul A. Sprengeler

研究成果: Article査読

40 被引用数 (Scopus)

抄録

Lactone (+)-12 is envisioned as the precursor to the F—G—H rings of penitrem D (4) in our ongoing synthetic venture. The efficient, stereocontrolled introduction of the vicinal quaternary methyl groups present the major challenge in the construction of this subunit. Our first route to (±)-12 was marked by low overall yield (<2%) and the instability of several key intermediates; these deficiencies weee rectified in a second-generation approach that produced optically active material (18 steps from 19a, 2.1% overall). The successful strategies exploited enolate generation via either conjugate additions to αpha;,β-enones or the Evans oxy-Cope rearrangement as key regiochemical control elements.

本文言語English
ページ(範囲)7837-7848
ページ数12
ジャーナルJournal of Organic Chemistry
60
24
DOI
出版ステータスPublished - 1995 12月 1
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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