Total Synthesis of <i>dl</i>-Atisine

Nagata, Wataru; Sugasawa, Tsutomu; Narisada, Masayuki; Wakabayashi, Toshio; Hayase, Yoshio

doi:10.1021/ja00982a036

Cited by 71 publications

(13 citation statements)

References 4 publications

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“…The C 20 -diterpenoid alkaloids have also served as classic targets in natural product synthesis, resulting in the total syntheses of natural products within the atisine (1), [13][14][15][16][17][18] veatchine (5), [19][20][21][22][23] and napelline (6) [24,25] subclasses. Despite this progress, synthetic efforts toward the hetisine subclass (4) have been comparatively sparse.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthetic Access to the Hetisine Alkaloids: Total Synthesis of (+)‐Nominine

Peese

Gin

2008

Chemistry A European J

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A dual cycloaddition strategy for the synthesis of the hetisine alkaloids has been developed, illustrated by a concise asymmetric total synthesis of (+)-nominine (7). The approach relies on an early-stage intramolecular 1,3-dipolar cycloaddition of a 4-oxido-isoquinolinium betaine dipole with an enenitrile dipolarophile. Subsequent late-stage pyrrolidine-induced dienamine isomerization/DielsAlder cascade allows for rapid construction of the carbon-nitrogen polycyclic skeleton within this class of C 20 -diterpenoid alkaloids.

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Section: Introductionmentioning

confidence: 99%

Asymmetric Synthetic Access to the Hetisine Alkaloids: Total Synthesis of (+)‐Nominine

Peese

Gin

2008

Chemistry A European J

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“…As indicated by the biogenetic considerations,amajority of the earliest synthetic endeavors were concentrated on the relatively simple alkaloids of atisine-and veatchine-types.Capitaliz-ing on Pelletier's partial synthesis (intermediates 13-15), [21] three groups (Nagata, [22] Masamune, [23] and Wiesner [24] )r ealized the formal synthesis of atisine in the 1960s,w ith another one described in 1988 by Fukumoto and co-workers (Scheme 1). [25] Xiao - It is noteworthy that Fukumoto's group also achieved an enantioselective formal synthesis of atisine employing al ipase-catalyzed kinetic resolution.…”

Section: Formalsynthesis Of Atisinementioning

confidence: 99%

Ongoing Pursuit of Diterpenoid Alkaloids: A Synthetic View

Liu

Qin

2015

Asian J Org Chem

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The incorporation of nitrogen atoms into policyclic diterpenes has led to one of the most fascinatingg roup of natural products with cage-like structures:d iterpenoid alkaloids. Their singular architectural features and significant bioactivitiesm ade them highly pursued targets amongst the synthetic community over decades. At otal of seven types of diterpenoid alkaloid molecules have been synthesized thus far,a nd the research in this area experiencedanew climax in the past five years. With ab rief overview and summary of the historic achievements, this Focus Review particularly covers the recent,post-2010 advances in the field of diterpenoid alkaloid synthesis, highlighting the utilizationofinnovative synthetic methods and strategies. Despite numerous achievements, there are stillanumber of such alkaloids with differenta nd uniques tructural types waiting to be accomplished, implying that the pursuit is far from ending.

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“…Its first total synthesis was completed in 1963 by Nagata 56 and constituted a formal total synthesis by intercepting Pelletier’s intermediate from a prior semisynthesis in 1956. 57 Several syntheses followed, but the most recent was reported by Ihara 25 years later in 1988.…”

Section: Diterpenoid Alkaloidsmentioning

confidence: 99%

Terpenoid‐Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis

Cherney

Baran

2011

Israel Journal of Chemistry

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Terpenes and alkaloids are ever-growing classes of natural products that provide new molecular structures which inspire chemists and possess a broad range of biological activity. Terpenoid-alkaloids originate from the same prenyl units that construct terpene skeletons. However, during biosynthesis, a nitrogen atom (or atoms) is introduced in the form of β-aminoethanol, ethylamine, or methylamine. Nitrogen incorporation can occur either before, during, or after the cyclase phase. The outcome of this unique biosynthesis is the formation of natural products containing unprecedented structures. These complex structural motifs expose current limitations in organic chemistry, thus providing opportunities for invention. This review focuses on total syntheses of terpenoid-alkaloids and unique issues presented by this class of natural products. More specifically, it examines how these syntheses relate to the way terpenoid-alkaloids are made in Nature. Developments in chemistry that have facilitated these syntheses are emphasized, as well as chemical technology needed to conquer those that evade synthesis.

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Total Synthesis of dl-Atisine

Cited by 71 publications

References 4 publications

Asymmetric Synthetic Access to the Hetisine Alkaloids: Total Synthesis of (+)‐Nominine

Asymmetric Synthetic Access to the Hetisine Alkaloids: Total Synthesis of (+)‐Nominine

Ongoing Pursuit of Diterpenoid Alkaloids: A Synthetic View

Terpenoid‐Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis

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