Journal ArticleDOI
[3,3]-Sigmatropic rearrangements in indoloazabicyclo[3.3.1]nonene systems. Reversal of the stereofacial selectivity in the Claisen vs. the ortho ester Claisen rearrangement
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This article is published in Journal of the American Chemical Society.The article was published on 1989-10-01. It has received 15 citations till now. The article focuses on the topics: Sigmatropic reaction & Carroll rearrangement.read more
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Journal ArticleDOI
General Approach for the Synthesis of Sarpagine Indole Alkaloids. Enantiospecific Total Synthesis of (+)-Vellosimine, (+)-Normacusine B, (−)-Alkaloid Q3, (−)-Panarine, (+)-Na-Methylvellosimine, and (+)-Na-Methyl-16-epipericyclivine
Jianming Yu,Wang T,Liu X,Jeffrey R. Deschamps,Judith L. Flippen-Anderson,Liao X,James M. Cook +6 more
TL;DR: The first total synthesis of (+)-Na-methyl-16-epipericyclivine was completed [from d-(+)-tryptophan methyl ester] in an overall yield of 42% (eight reaction vessels) and the optical rotation obtained on this material confirmed that the reported optical rotation was biogenetically unreasonable.
Book ChapterDOI
7.2 – Claisen Rearrangements
TL;DR: In this paper, a survey of variants of the Claisen rearrangement that are of general use in stereoselective organic synthesis is presented, highlighting the influence of steric and electronic parameters on transition state geometries.
Journal ArticleDOI
General Approach for the Synthesis of Ajmaline/Sarpagine Indole Alkaloids: Enantiospecific Total Synthesis of (+)-Ajmaline, Alkaloid G, and Norsuaveoline via the Asymmetric Pictet−Spengler Reaction
Jin Li,Tao Wang,Peng Yu,A. Peterson,Robert W. Weber,D. Soerens,D. Grubisha,Dennis W. Bennett,James M. Cook +8 more
TL;DR: In this article, a general approach (oxyanion-Cope strategy) for the synthesis of sarpagine/ajmaline indole alkaloids has been developed, which employs a stereospecific Pictet−Spengler/Dieckmann protocol to prepare the key intermediate, (−)-Nb-benzyl tetracyclic ketone.
Journal ArticleDOI
Regiospecific, enantiospecific total synthesis of the 12-alkoxy-substituted indole alkaloids, (+)-12-methoxy-Na-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline.
TL;DR: The enantiospecific synthesis of 7-methoxy-d-tryptophan was completed by combination of the Larock heteroannulation process with a Schöllkopf-based chiral auxiliary in good yield and an enolate-driven palladium-catalyzed cross coupling processes served as key steps.
Journal ArticleDOI
Enantiospecific total synthesis of the sarpagine related indole alkaloids talpinine and talcarpine as well as the improved total synthesis of alstonerine and anhydromacrosalhine-methine via the asymmetric Pictet-Spengler reaction.
TL;DR: A convenient synthetic route for the enantiospecific, stereospecific preparation of the key intermediate (-)-N(a)-H, N(b)-benzyl tetracyclic ketone 15a via the asymmetric Pictet-Spengler reaction on a multihundred-gram scale has been developed.
Related Papers (5)
General approach to the synthesis of macroline-related alkaloids. Stereospecific total synthesis of (-)-alstonerine
L. H. Zhang,J. M. Cook +1 more