Total Synthesis of (±)-Mersicarpine

Magolan, Jakob; Carson, Cheryl A.; Kerr, Michael A.

doi:10.1021/ol800259s

Cited by 142 publications

(93 citation statements)

References 12 publications

(13 reference statements)

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“…These conditions simultaneously deprotected the amino group, so the Boc unit had to be reinstalled. Compound 179 , thus obtained, had already been converted into (±)‐mersicarpine 180 by Kerr and coworkers in three steps, so the sequence in Scheme represents a formal synthesis of this unusual Kopsia alkaloid …”

Section: Applications To Synthesismentioning

confidence: 89%

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On the Strategic Impact of the Degenerative Transfer of Xanthates on Synthetic Planning

Quiclet‐Sire

Zard

2016

Israel Journal of Chemistry

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The present brief account relates synthetic endeavours revolving around a novel chemistry of xanthates (dithiocarbonates) being developed in our group. The degenerative reversible transfer of xanthates has a unique ability to store reactive radicals in a dormant form, and thereby to enhance their lifetime in a concentrated medium, while at the same time, regulating their absolute and relative concentrations. It allows intermolecular radical additions even to unactivated alkenes, and can promote otherwise sluggish radical processes, such as 5‐endo, 6‐exo, 6‐endo, 7‐endo, and 8‐endo cyclisations, as well as ring closures on (hetero)aromatic structures. This chemistry has proved remarkably versatile and powerful, both for solving synthetic problems and for the industrial production of block copolymers through the RAFT/MADIX technology.

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Section: Applications To Synthesismentioning

confidence: 89%

“…Compound 179, thus obtained, had already been converted into (AE)-mersicarpine 180 by Kerr and coworkers in three steps,s ot he sequence in Scheme 19 represents af ormal synthesis of this unusual Kopsia alkaloid. [54] Scheme 18. An alliance with the alkylative Birch reduction.…”

Section: Reactions Involving Crossover To the Cationic Manifoldmentioning

confidence: 99%

On the Strategic Impact of the Degenerative Transfer of Xanthates on Synthetic Planning

Quiclet‐Sire

Zard

2016

Israel Journal of Chemistry

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“…Later, Kerr et al . developed an intramolecular version of this reaction ( A to B , Figure ), which was applied to the total syntheses of mersicarpine and alsmaphorazine D . In an attempt to assemble welwitindolinone, the Rawal group observed that manganese(III)‐mediated oxidative cyclization between indole part and a tethered β‐ketoester unit occurred either at the indole C4‐position ( C to D ) or at the indole C2‐position ( C to E ) depending on the substituents at the indole C2‐position .…”

Section: Figurementioning

confidence: 99%

Total Synthesis of Lapidilectine B Enabled by Manganese(III)‐Mediated Oxidative Cyclization of Indoles

Gao

Fan

Geng

et al. 2018

Chemistry A European J

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A novel manganese(III)-mediated oxidative cyclization of readily accessible 1,2,3-trisubstituted indoles is described. This unprecedented method enabled the efficient construction of a complex polycyclic scaffold bearing a spiro-indoline motif and a lactone moiety in one step. Its synthetic utility was demonstrated in the total synthesis of lapidilectine B (in 18 steps) by employing a strategic regioselective ring-expansion and a silver-promoted allenic amine cyclization as the additional key elements.

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“…This intriguing molecule has attracted much attention, and four total syntheses, including ours, have been reported to date. [2][3][4][5] Chart 1 depicts our synthesis of mersicarpine (1). First, the quaternary carbon was constructed according to d'Angelo's procedure.…”

Section: Synthesis Of Mersicarpinementioning

confidence: 99%

Synthesis of Natural Products with Polycyclic Systems

Yokoshima

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herein we present our unique strategies to synthesize natural products. To prepare mersicarpine, an atypical indole alkaloid, our procedure features an Eschenmoser-Tanabe fragmentation to synthesize an alkyne unit, a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization to construct the indole skeleton, and a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Additionally, we synthesized a frog poison, histrionicotoxin, via a chirality transfer from an allenylsilane to prepare a pseudosymmetrical dienyne, dienyne metathesis to produce an optically active bicyclo [5.4.0] system, and an asymmetric propargylation. To synthesize lyconadin A, a Lycopodium alkaloid, a combination of an azaPrins reaction and electrocyclic ring opening constructed the highly fused tetracyclic compound. The synthesis of isoschizogamine features a facile construction of the carbon framework through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.

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Total Synthesis of (±)-Mersicarpine

Cited by 142 publications

References 12 publications

On the Strategic Impact of the Degenerative Transfer of Xanthates on Synthetic Planning

On the Strategic Impact of the Degenerative Transfer of Xanthates on Synthetic Planning

Total Synthesis of Lapidilectine B Enabled by Manganese(III)‐Mediated Oxidative Cyclization of Indoles

Synthesis of Natural Products with Polycyclic Systems

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