Tremorgenic indole alkaloids. 9. Asymmetric construction of an advanced FGH-ring lactone precursor for the synthesis of penitrem D

AB Smith III, EG Nolen, R Shirai, FR Blase…

Index: Smith, Amos B.; Nolen, Ernest G.; Shirai, Ryuichi; Blase, Frances R.; Ohta, Mitsuaki; et al. Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 7837 - 7848

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Citation Number: 34

Abstract

Lactone (+)-12 is envisioned as the precursor to the FGH 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 (f1-12 was marked by low overall yield (< 2% 1 and the instability of several key intermediates; these deficiencies were rectified in a second-generation approach that ...