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

Full Text: HTML

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 ...

Related Articles:

Synthesis and pharmacological evaluation of hexahydrofluorenamines as noncompetitive antagonists at the N-methyl-D-aspartate receptor

[Hays, Sheryl J.; Novak, Perry M.; Ortwine, Daniel F.; Bigge, Christopher F.; Colbry, Norman L.; et al. Journal of Medicinal Chemistry, 1993 , vol. 36, # 6 p. 654 - 670]

Regiochemical control of the ring-opening of 1, 2-epoxides by means of chelating processes. 2. Synthesis and reactions of the cis-and trans-oxides of 4-[(benzyloxy) …

[Chini, Marco; Crotti, Paolo; Flippin, Lee A.; Macchia, Franco; Pineschi, Mauro Journal of Organic Chemistry, 1992 , vol. 57, # 5 p. 1405 - 1412]

Regiochemical control of the ring-opening of 1, 2-epoxides by means of chelating processes. 2. Synthesis and reactions of the cis-and trans-oxides of 4-[(benzyloxy) …

[Chini, Marco; Crotti, Paolo; Flippin, Lee A.; Macchia, Franco; Pineschi, Mauro Journal of Organic Chemistry, 1992 , vol. 57, # 5 p. 1405 - 1412]

More Articles...